Preparing From A Phenol And An Aldehyde Or Ketone Patents (Class 568/727)
  • Patent number: 5516441
    Abstract: A metal salt or boron compound of a hydrocarbyl-substituted aromatic hydroxy compound having at least two hydroxy-substituted aromatic rings bridged by sulfur, where at least one aromatic ring bears a substituent ortho to a hydroxy group, provides a useful lubricant additive. The substituent on the aromatic ring is an .alpha.-hydroxy aliphatic hydrocarbyl group or a --C(O)R.sup.2 group, where R.sup.2 is hydrogen or aliphatic hydrocarbyl. Preferred salts are magnesium.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: May 14, 1996
    Assignee: The Lubrizol Corporation
    Inventor: Richard A. Denis
  • Patent number: 5512700
    Abstract: A process for the purification of a crude bisphenol comprises the following steps:(1) preparing a mixture comprising from about 35 to about 70% of a crude bisphenol and from about 65 to about 30% of water, by the total weight of bisphenol and water, without addition of a substantial amount of an organic solvent or an alkaline compound, at a pressure above atmospheric and a temperature above about 100.degree. C.,(2) crystallizing bisphenol at a pressure below atmospheric,(3) separating crystalline bisphenol from the mother liquor,(4) dividing at least a portion of the mother liquor into a bisphenol-rich oil phase and a water-rich phase,(5) preparing a mixture comprising at least a portion of the bisphenol-rich oil phase, water and optionally an additional amount of crude bisphenol at a pressure above atmospheric and a temperature above about 100.degree. C.,(6) cooling the mixture and crystallizing bisphenol; and(7) separating crystalline bisphenol from the mother liquor.
    Type: Grant
    Filed: March 10, 1995
    Date of Patent: April 30, 1996
    Assignee: Dow Deutschland Inc.
    Inventors: Emil Patrascu, Karl Kraehling, Jochen Gressmann
  • Patent number: 5504251
    Abstract: This invention relates to processing of a mixture of tars produced in phenol manufacture and in bisphenol manufacture. The heating of a bottom liquid from a bisphenol-A process together with phenol tar from in a cumene-to-phenol process in a distillation column-type thermal cracking reactor at 290.degree.-360.degree. C. at a mass ratio of 1:(1-10) is employed. The process is carried out by feed entering into the middle of the column and valuable products removed as overhead.
    Type: Grant
    Filed: March 9, 1995
    Date of Patent: April 2, 1996
    Assignee: General Electric Company
    Inventors: Arkady S. Dyckman, Andrey V. Zinenkov, Boris I. Gorovits, Valentina Y. Shefter, John W. Fulmer, William D. Kight
  • Patent number: 5475154
    Abstract: Low-color bisphenols may be produced by condensing phenol with ketones in the presence of a strong-acid cation exchange resin acting as an acid catalyst for the condensation reaction, and of a small amount, relative to the acid catalyst, of a weak-base anion exchange resin.
    Type: Grant
    Filed: March 10, 1994
    Date of Patent: December 12, 1995
    Assignee: Rohm and Haas Company
    Inventors: Eric G. Lundquist, Michael P. Bigwood
  • Patent number: 5475155
    Abstract: 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: Grant
    Filed: January 18, 1995
    Date of Patent: December 12, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Maria I. Villarreal, David A. Carr
  • Patent number: 5463140
    Abstract: 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: Grant
    Filed: August 31, 1994
    Date of Patent: October 31, 1995
    Assignee: The Dow Chemical Company
    Inventors: Richard M. Wehmeyer, Marlin E. Walters, Emmett L. Tasset, Steven L. Brewster
  • Patent number: 5455282
    Abstract: The invention relates to repeatedly regeneratable ion exchanger resins with a thin covering of alkyl-SH groups.
    Type: Grant
    Filed: January 30, 1995
    Date of Patent: October 3, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Berg, Georg Malamet, Franz Backes, Alfred Eitel, Claus Wulff
  • Patent number: 5434316
    Abstract: Bisphenol-A produced by the condensation of acetone and phenol is freed of contaminant co-products by melting and crystallization in and from water. The final washing, in hot water, cleanses the crystal surfaces of remaining contaminants without the need for organic solvents.
    Type: Grant
    Filed: July 28, 1994
    Date of Patent: July 18, 1995
    Assignee: General Electric Company
    Inventor: Gaylord M. Kissinger
  • Patent number: 5428075
    Abstract: A method is provided for regenerating deactivated sulfonated aromatic organic ion-exchange resin beds, such as a polystyrene ion-exchange resin bed, having chemically combined amino organo mercaptan groups with anhydrous phenol at an elevated temperature.
    Type: Grant
    Filed: May 2, 1994
    Date of Patent: June 27, 1995
    Assignee: General Electric Company
    Inventors: Eric J. Pressman, Sheldon J. Shafer
  • Patent number: 5414151
    Abstract: A method is provided for making bisphenol by condensing a ketone and a phenol in the presence of a sulfonated aromatic organic polymeric ion-exchange catalyst having aminoorganomercaptan groups using a phenol having less than 1 ppm of hydroxyacetone.
    Type: Grant
    Filed: May 2, 1994
    Date of Patent: May 9, 1995
    Assignee: General Electric Company
    Inventors: Eric J. Pressman, Sheldon J. Shafer
  • Patent number: 5414152
    Abstract: The addition of 3-mercaptopropionic acid or the organic ester thereof to the reaction mixture slows the rate of deactivation of cationic catalyst resins containing mercaptan promoter sites, during preparation of bisphenols by the condensation of a ketone with a phenol.
    Type: Grant
    Filed: May 10, 1994
    Date of Patent: May 9, 1995
    Assignee: General Electric Company
    Inventor: Michael J. Cipullo
  • Patent number: 5395915
    Abstract: Herein disclosed is a method for simultaneously preparing a highly pure bisphenol F and/or a bisphenol F for general use and a novolak phenol resin and/or a high molecular weight novolak phenol resin comprising the steps of:(1) a preparation step comprising reacting phenol with formaldehyde in the presence of an acid catalyst and removing the acid catalyst, water and the unreacted phenol from the resulting reaction product to give a crude bisphenol F;(2) a distillation step comprising distilling a part of the crude bisphenol F to give a highly pure bisphenol F, as a distillate, having a binuclear moiety-content of not less than 95% by weight and a novolak phenol resin, as a still-bottom product, having a binuclear moiety-content of not more than 15% by area;(3) a step for mixing the highly pure bisphenol F with the remaining crude bisphenol F to give a bisphenol F for general use; and(4) a step for polymerizing the novolak phenol resin with formaldehyde in the presence of an acid catalyst to give a high molec
    Type: Grant
    Filed: August 12, 1993
    Date of Patent: March 7, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shigeru Iimuro, Satoru Ito, Tomoko Takashima, Takashi Kitamura
  • Patent number: 5387725
    Abstract: Compounds having acidic protons and a molecular structure which can delocalize the electron density of the conjugate base (target compounds) are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylammonium hydroxide. Chlorinated products, preferably gem-dichloro compounds, are produced. The gem-dichloro compounds are useful for alkylation of aromatic compounds. For instance fluorene is chlorinated to form 9,9-dichlorofluorene which is reacted with such compounds as phenol or aniline to form such compounds as 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(aminophenyl)fluorene, or 9-aminophenyl-9-chlorofluorene.
    Type: Grant
    Filed: July 12, 1993
    Date of Patent: February 7, 1995
    Assignee: The Dow Chemical Company
    Inventors: Marlin E. Walters, W. Frank Richey, Katherine S. Clement, Steven L. Brewster, Emmett L. Tasset, Paul M. Puckett, V. Rao Durvasula, Hong A. Nguyen
  • Patent number: 5382712
    Abstract: High quality bisphenol A is produced from a neutral crystalline adduct of bisphenol A and phenol by fusing the adduct in an atmosphere having a maximum oxygen content of 0.005% by volume, followed by evaporation of liberated phenol. The crystalline adduct may be mixed with an aliphatic carboxylic acid before the fusion to reduce the coloring of the product. When an acidic crystalline adduct is used, the use of a strong alkali salt of an aliphatic carboxylic acid is suitably used. Interior surfaces of the apparatuses for carrying out the fusion and evaporation are desirably washed with an organic solvent to remove oxygen therefrom. The evaporation of phenol is suitably performed by two stage steam stripping wherein a used stripping gas obtained in the second stage is employed as a stripping gas in the first stage while steam is used as the stripping gas in the second stage.
    Type: Grant
    Filed: April 18, 1994
    Date of Patent: January 17, 1995
    Assignee: Chiyoda Corporation
    Inventors: Sachio Asaoka, Tetsuo Maejima, Kouji Sakashita, Noriyuki Yoneda, Makoto Yasui, Nobuhiro Onda, Tsuneo Watanabe, Nobuo Moriya, Akio Shindo, Hiroaki Nishijima, Athumi Kukidome, Ryuichi Inaba, Takashi Imazeki, Kaoru Shimogawara
  • Patent number: 5362900
    Abstract: A method comprising purifying impure bisphenol-A by fractional melt crystallization in a falling film dynamic crystallizer.
    Type: Grant
    Filed: August 18, 1993
    Date of Patent: November 8, 1994
    Assignees: General Electric Co., Sulzer Canada, Inc.
    Inventors: Gaylord M. Kissinger, Nicholas P. Wynn
  • Patent number: 5345001
    Abstract: An aqueous resol solution produced by an alkaline condensation of a phenolic compound with an aldehyde in a molar ratio of 1:1.5 to 2.5 with an alkali metal content of 1 to 5.0% by weight of the reaction solution, neutralizing the solution after the end of condensation at least partially with an aromatic hydroxy carboxylic acid at a temperature not greater than 50.degree. C. and then concentrating the reaction mixture which is readily dilutable with water.
    Type: Grant
    Filed: August 23, 1993
    Date of Patent: September 6, 1994
    Assignee: Rutgerswerke Aktiengesellschaft AG
    Inventors: Stephan Schroter, Achim Hansen, Arno Gardziella, Peter Adolphs
  • Patent number: 5345000
    Abstract: High purity, crystalline adduct of bisphenol A and phenol is produced multi-stage crystallization of a phenolic slurry of bisphenol A with a crystal separation and washing step being interposed between each of the two stages. Each of the crystallization stage includes a series of crystallization towers operated at decreasing temperatures. The crystallization of the slurry is performed by continuously discharging a portion of the slurry from each of the crystallization towers, introducing the discharged slurry into one or more coolers and then recycling the cooled slurry to the tower. Another portion of the slurry in each crystallization slurry is continuously discharged, heated for dissolving fine crystals of the adduct and then recycled to the crystallization tower so that large crystals are grown in each of the crystallization steps. An apparatus having a plurality of coolers and suitable for effecting the above crystallization is also disclosed.
    Type: Grant
    Filed: March 3, 1993
    Date of Patent: September 6, 1994
    Assignee: Chiyoda Corporation
    Inventors: Nobuo Moriya, Keiji Shimoda, Sachio Asaoka, Takao Kameda, Kouji Sakashita, Tetsuo Maejima, Makoto Yasui, Hiroaki Nishijima, Nobuhiro Onda, Takeshi Kouzaki
  • Patent number: 5336813
    Abstract: A process comprising the addition of a degradation inhibiting effective amount of an amine having a boiling point above that of the phenol used in the process to a composition comprising the said phenol and a bisphenol, the addition occurring prior to a procedure which subjects the bisphenol to substantial heat, said bisphenol produced from an acidic ion exchange resin catalyzed reaction of the said phenol and a ketone or aldehyde.
    Type: Grant
    Filed: January 29, 1993
    Date of Patent: August 9, 1994
    Assignee: General Electric Company
    Inventors: Michael J. Cipullo, John W. Fulmer
  • Patent number: 5324867
    Abstract: High quality bisphenol A is produced from a neutral crystalline adduct of bisphenol A and phenol by fusing the adduct in an atmosphere having a maximum oxygen content of 0.005% by volume, followed by evaporation of liberated phenol. The crystalline adduct may be mixed with an aliphatic carboxylic acid before the fusion to reduce the coloring of the product. When an acidic crystalline adduct is used, the use of a strong alkali salt of an aliphatic carboxylic acid is suitably used. Interior surfaces of the apparatuses for carrying out the fusion and evaporation are desirably washed with an organic solvent to remove oxygen therefrom. The evaporation of phenol is suitably performed by two stage steam stripping wherein a used stripping gas obtained in the second stage is employed as a stripping gas in the first stage while steam is used as the stripping gas in the second stage.
    Type: Grant
    Filed: July 13, 1992
    Date of Patent: June 28, 1994
    Assignee: Chiyoda Corporation
    Inventors: Sachio Asaoka, Tetsuo Maejima, Kouji Sakashita, Noriyuki Yoneda, Makoto Yasui, Nobuhiro Onda, Tsuneo Watanabe, Nobuo Moriya, Akio Shindo, Hiroaki Nishijima, Athumi Kukidome, Ryuichi Inaba, Takashi Imazeki, Kaoru Shimogawara
  • Patent number: 5315042
    Abstract: Product quality productivity of continuous bisphenol-A (BPA) are increased by increasing the flow rate of reactants through the reactor and decreasing % acetone conversion in the presence of an ion exchange resin catalyst and an optional free mercaptan promoter.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: May 24, 1994
    Assignee: General Electric Company
    Inventors: Michael J. Cipullo, Gaylord M. Kissinger, Isabel M. Matos
  • Patent number: 5304688
    Abstract: A process for the preparation of bishydroxy aromatic compounds, such as 9,9-bis(4-hydroxyphenyl)fluorene, involving contacting a ketone, such as fluorenone, with phenol or substituted phenol in the presence of a mercaptan cocatalyst and a solid superacid catalyst of Hammett acid strength H.sub.0 greater than about -13.0. Solid superacid catalysts include the sulfates, sulfated oxides, sulfated oxyhydroxides, and sulfated oxysilicates of aluminum, tin, and the Group IVA metals, such as zirconium, as well as mixed metal oxides, such as tungsten-zirconium oxides. Isolated yields are high for 9,9-bis(4-hydroxyphenyl)fluorene.
    Type: Grant
    Filed: April 13, 1993
    Date of Patent: April 19, 1994
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, Muthiah N. Inbasekaran
  • Patent number: 5302774
    Abstract: The invention relates to a process for the production of bisphenols from acetone and phenols in the presence of sulfonic acid ion exchanger resins modified with alkyl-SH groups, in which 0.6 to 5% by weight H.sub.2 O is added to the mixture of phenol and acetone before the reaction.
    Type: Grant
    Filed: August 9, 1993
    Date of Patent: April 12, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Berg, Hans-Josef Buysch, Alfred Eitel, Gerhard Fennhoff, Otto Immel, Ralf Pakull, Bernhard Wehrle, Claus Wulff
  • Patent number: 5300700
    Abstract: The invention relates to a special process for the production of high-purity bisphenol A from acetone and phenol in the presence of acidic catalysts.
    Type: Grant
    Filed: April 20, 1993
    Date of Patent: April 5, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Georg Malamet, Hans-Peter Wirges, Claus Wulff, Alfred Eitel
  • Patent number: 5288926
    Abstract: Bisphenols are prepared bya) reacting a phenolic compound with a carbonyl compound in a reaction mixture, containing the carbonyl compound, a stoichiometric excess of the phenolic compound and a catalyst, to produce a product mixture containing a bisphenol,b) separating bisphenol from the product mixture to leave a mother liquor andc) recycling at least a portion of the mother liquor to the reaction mixture.At least a portion of the phenolic compound is contacted with a strongly acidic cation exchange resin and a strongly basic anion exchange resin before the phenolic compound is used in the reaction step a) and/or at least a portion of the product mixture and/or at least a portion or the mother liquor is contacted with a strongly acidic cation exchange resin and a strongly basic anion exchange resin before mother liquor is recycled to the reaction mixture.
    Type: Grant
    Filed: February 4, 1993
    Date of Patent: February 22, 1994
    Assignee: The Dow Chemical Company
    Inventors: Emil Patrascu, Dieter Tank, Jochen Gressmann, Johann-Wilhelm Frey, Ulrich Wallbaum
  • Patent number: 5284981
    Abstract: This invention relates to a catalyst modified with mercapto amines, its preparation and its use for the preparation of bisphenols.
    Type: Grant
    Filed: May 1, 1990
    Date of Patent: February 8, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Rudolph, Norbert Bachem, Claus Wulff
  • Patent number: 5276213
    Abstract: Dihydroxydiphenyl bicycloalkanes characterized in that they contain 9 to 13 ring C atoms in the bicycloaliphatic component are disclosed. The disclosed compounds were found to be suitable for the preparation of high molecular weight, thermoplastic polycarbonate resins having favorable properties.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: January 4, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Volker Serini, Uwe Westeppe, Gerd Fengler, Manfred Hajek, Carl Casser, Helmut Waldmann
  • Patent number: 5248839
    Abstract: A preparation process of high purity bisphenol A from phenol and acetone with a continuous or batch type reactor by on-line estimating with a computer the composition of the reaction mixture and saturated dissolving temperature of bisphenol A under the reaction conditions and by automatically controlling the reaction conditions and liquid transfer conditions of the reaction mixture to the next step. The process does not form crystals of bisphenol A-phenol adduct in the reactor and cooler. A maximum rate of reaction can be obtained. Consequently, fluctuation of reaction temperature can be prevented and the amount of impurities formed is small. The discharge operation of the reaction mixture from the reactor can be carried out steadily and with ease, and does not disturb the operation of successive steps.
    Type: Grant
    Filed: April 7, 1992
    Date of Patent: September 28, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shigeru Iimuro, Akira Yamada, Kenichi Ohmura, Toshio Houri, Tsuguo Kawamura
  • Patent number: 5248838
    Abstract: A process for preparing bisphenol fluorene products which comprises reacting fluorenone with a phenol compound in the presence of an acidic condensing agent in a solution of an organic liquid wherein the bisphenol fluorene compound is insoluble and recovering the obtained bisphenol fluorene product from the reaction mixture.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: September 28, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Sergio Massirio, Mauro Besio, Marcello Gagliano, Brunella Fornasari, Angelo Vallarino, Piera Di Mito
  • Patent number: 5233096
    Abstract: Strongly acidic cation-exchange resin beads made by functionalizing jetted, suspension-polymerized, crosslinked, styrenic copolymer beads with sulfonic acid groups produce an unexpectedly high level of conversion when catalyzing condensation reactions, particularly the condensation of phenol with aldehydes or ketones to form bisphenols.
    Type: Grant
    Filed: July 13, 1992
    Date of Patent: August 3, 1993
    Assignee: Rohm and Haas Company
    Inventor: Eric G. Lundquist
  • Patent number: 5220079
    Abstract: A process for preparing phenols with high selectivities, comprising reacting a phenol compound and a formaldehyde source with a quaternary ammonium as a counter cation of a phenol anion in the presence of an alcoholic organic solvent.
    Type: Grant
    Filed: April 24, 1992
    Date of Patent: June 15, 1993
    Assignee: Mitsubishi Petrochemical Company Limited
    Inventors: Hiroshi Iwane, Takahiro Sugawara, Naoki Suzuki, Kimiko Kaneko
  • Patent number: 5210329
    Abstract: A process which comprises reacting phenol and acetone in the presence of an acidic catalyst and thereaftera. isolating first major portion of bisphenol-A, therefore forming a purge stream comprising bisphenol-A, bisphenol-A isomers and tar,b. adding or taking from the said purge stream, if necessary, sufficient phenol so as to bring the purge stream ratio of phenol to bisphenol-A to about 5:1 to 15:1 based on moles, thereby forming an altered purge stream,c. bringing the temperature of the altered stream to a range of about 30.degree.-50.degree. C.,d. maintaining the temperature of the altered stream at about 30.degree.-50.degree. C. until about 60-85% of the bisphenol-A crystallizes as a bisphenol-A/phenol 1:1 molar adduct,e. separating the adduct from its mother liquor.
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: May 11, 1993
    Assignee: General Electric Company
    Inventors: Isabel M. Gomes de Matos, Allen Wai-Kee Ko
  • Patent number: 5198591
    Abstract: The invention relates to a process for obtaining a high purity bisphenol from a post-reaction mixture resulting from the step of synthesis of phenol and acetone in the presence of a strong acid cation exhanger catalyst, by the way of crystallation and separation by distillation followed by recovery of bisphenol-A from the step of thermal catalytic decomposition of by product of the principal process technology in a multistage process.
    Type: Grant
    Filed: November 22, 1991
    Date of Patent: March 30, 1993
    Assignees: Instytut Ciezkiej Syntezy Organicznej "Blachownia", Zaklady Chemiczne "Blachownia", ABB Lummus Crest Inc.
    Inventors: Maciej Kiedik, Jozef Kolt, Jerzy Marszycki, Eugeniusz Zajac, Teodor Bek, Zbigniew Swiderski, Anna Rzodeczko, Jerzy Mroz, Janina Olkowska
  • Patent number: 5191128
    Abstract: Tetraphenolic compounds such as the tetraphenol of ethane and the tetraphenol of xylene can be prepared in a ketone/alcohol solvent medium using a cation exchange resin catalyst.
    Type: Grant
    Filed: March 12, 1992
    Date of Patent: March 2, 1993
    Assignee: Shell Oil Company
    Inventor: Simon M. Li
  • Patent number: 5169990
    Abstract: In the production of 9,9-bis-(4-hydroxphenyl)-fluorene by condensation by fluorenone and phenol in a molar ratio of 1:4 to 1:8 at 30.degree. to 90.degree. C. in the presence of gaseous hydrogen chloride and .beta.-mercapto-propionic acid as catalyst, the improvement comprising mixing the completed reaction mixture with a polyalkylene glycol, distilling excess phenol from the mixture, and mixing the distillation residue with a solvent miscible with the polyalkylene glycol, recovering the crystallized product, suspending the crystallized product in water and heating the suspension to obtain highly pure 9,9-bis-(4-hydroxyphenyl)-fluorene as white crystals.
    Type: Grant
    Filed: February 11, 1992
    Date of Patent: December 8, 1992
    Assignee: Rutgerswerke Aktiengesellschaft
    Inventors: Winfried Orth, Emmerich Pastorek, Wolfgang Weiss, Hans W. Kleffner
  • Patent number: 5169992
    Abstract: Disclosed is a one step method for synthesis of bisphenol A which comprises reacting phenol with acetone in the presence of a catalyst comprising an acidic montmorillonite clay having the structure:M.sub.x/n.sup.n+ .multidot.yH.sub.2 O(Al.sub.4-x Mg.sub.x) (Si.sub.8) O.sub.20 (OH).sub.4where M represent the interlamellar, balancing cation (normally sodium or lithium), and x, y and n are integers, wherein the acidic clay has been pretreated with an acid and optionally has deposited thereon an acid selected from the group consisting hydrogen fluoride, a fluorosulfonic acid or a mineral acid, at a temperature of from 20.degree. C. to 200.degree. C. and a pressure of from near atmospheric to about 1000 psi.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: December 8, 1992
    Assignee: Texaco Chemical Company
    Inventor: John F. Knifton
  • Patent number: 5149886
    Abstract: In a process for the preparation of 9,9-bis-(4-hydroxyphenyl)-fluorene by condensing fluorenone and phenol in a molar ratio of 1:4 to 1:8 at 30.degree. to 90.degree. C. in the presence of gaseous hydrogen chloride and .beta.-mercapto-propionic acid catalyst, the improvement comprising distilling water of reaction and dissolved hydrochloric acid from the completed reaction mixture, dissolving the distillation residue in a nitrile, separating the crystallized adduct of nitrile and 9,9-bis-(4-hydroxphenyl)- fluorene from the nitrile and optionally dissociating the adduct to recover high purity 9,9-bis-(4-hydroxphenyl)- fluorene.
    Type: Grant
    Filed: February 11, 1992
    Date of Patent: September 22, 1992
    Assignee: Rutgerswerke AG
    Inventors: Winfried Orth, Emmerich Pastorek, Wolfgang Weiss, Hans W. Kleffner
  • Patent number: 5146007
    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 anhydrous comprises two steps to minimize resin degradation. In the first step, from 25 to 90 percent by weight of the resin associated water is removed by vaporization, and in the second step dehydration is completed by saturating the partially dehydrated catalyst with phenol. The advantage of the improvement in the process resides in a more efficient drying, requiring less time and minimal degradation of the resin structure.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: September 8, 1992
    Assignee: General Electric Company
    Inventor: Michael J. Cipullo
  • Patent number: 5118875
    Abstract: Additives of improving the low temperature flow properties and oxidative stability of hydrocarbon oils are disclosed, which comprise the alkylation of a phenol in the presence of a polar aprotic cosolvent to produce an essentially linear alkylated phenol which is condensed with an aldehyde to produce the low temperature flow improver wherein:(a) the polymer composition has a number average molecular weight of at least about 3,000 and a molecular weight distribution of at least about 1.5;(b) in the alkylated phenol reactant the alkyl groups (i) are essentially linear; (ii) have between 6 and 50 carbon atoms; and (iii) have an average number of carbon atoms between about 12 and 26; and(c) not more than about 10 mole percent of the alkyl groups on the alkylated phenol have less than 12 carbon atoms and not more than about 10 mole percent of the alkyl groups on the alkylated phenol have more than 26 carbon atoms.
    Type: Grant
    Filed: October 10, 1990
    Date of Patent: June 2, 1992
    Assignee: Exxon Chemical Patents Inc.
    Inventors: David J. Martella, John J. Jaruzelski, Frank J. Chen
  • Patent number: 5115084
    Abstract: A method for controlling the permeability of a petroleum-bearing subterranean formation including the steps of producing from biomass, a water-insoluble viscous biomass oil, and injecting the biomass oil into the petroleum bearing formation to decrease the permeability of at least some of the formation for altering flow paths through the formation to increase petroleum yield.
    Type: Grant
    Filed: January 29, 1991
    Date of Patent: May 19, 1992
    Assignee: Biocarbons Corporation
    Inventor: D. Andrew Himmelblau
  • Patent number: 5110994
    Abstract: The invention concerns a process for synthesizing 9,9-bis(hydroxyphenyl)fluorene by reacting fluorene with excess phenol using a liquid catalyst prepared by dissolving aluminum trichloride in an anhydrous organic solvent such as toluene evincing the property of an electron donor while hydrochloric-acid gas is being supplied. For the purpose of the synthesis, the fluorenone is dissolved for instance at 60.degree. C. in the liquid phenol and then the liquid catalyst is dripped into the agitated reaction mixture at such a rate that the temperature of the reaction mixture is kept below 60.degree. C. Following catalyst addition and subsequent after-reaction interval of several hours, the raw product is mixed with hot water and the excess phenol is removed by steam distillation. After signle-washing with water, the raw product is dissolved in hot acetone, allowed to crystallize, is filtered out and dried in vacuum. Lastly the raw product is recrystallized from 1,2-dichloroethane to form the pure product.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: May 5, 1992
    Assignee: ISONOVA Technische Innovationen G.m.b.H
    Inventor: Peter Fialla
  • Patent number: 5107036
    Abstract: A curing agent for an epoxy resin comprising (A) a polyhydric phenol obtainable by condensing a phenol compound and a hydroxybenzaldehyde and (B) a dihydric phenol, which gives a cured material of an epoxy resin having improved moisture and heat resistance and a small coefficient of linear thermal expansion.
    Type: Grant
    Filed: October 24, 1990
    Date of Patent: April 21, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Nobuyuki Nakajima, Shuichi Kanagawa, Hideshi Sakamoto, Noriaki Saito, Tadashi Ikushima
  • Patent number: 5105026
    Abstract: The present disclosure is directed to improving purity of a bisphenol product in a bisphenol by-product isomerization process wherein isomers of bisphenol are isomerized to the desired bisphenol product. During the isomerization, acidic resin fines elute from the acidic ion exchange resin catalyst into the reaction effluent. These resin fines can be filtered effectively and without contamination by a bed of solid particles such as alumina or carbon. The removal of resin fines improves the product quality and yield by eliminating resin particulates and reducing acid catalyzed cracking of bisphenols during purification and finishing steps.
    Type: Grant
    Filed: November 15, 1990
    Date of Patent: April 14, 1992
    Assignee: Shell Oil Company
    Inventors: Joseph B. Powell, Christopher W. Uzelmeier
  • Patent number: 5105027
    Abstract: Bisphenol A is prepared by condensing a stoichiometric excess of phenol with acetone in the presence of (a) a catalytically effective amount of an acid catalyst, e.g., benzenesulfonic acid, and (b) a co-catalytically effective amount of a functional polymer characteristically having the formula: ##STR1## in which m is 0 or 1, n is 0 or 1, p is 0 or 1, R.sup.1, R.sup.2 and R.sup.3, which may be identical or different, are each a hydrogen atom, a C.sub.1 -C.sub.6 alkyl radical or a phenyl radical optionally substituted by 1 or 2 hydroxyl or C.sub.1 -C.sub.4 alkoxy groups, and R.sup.4 is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl radical, or one of the groups: --CHO, --NO.sub.2, --CO.sub.2 H, --CO.sub.2 R.sup.5 wherein R.sup.5 is a C.sub.1 -C.sub.4 alkyl radical, or ##STR2## is the residue of a chloromethylated resin.
    Type: Grant
    Filed: February 28, 1991
    Date of Patent: April 14, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Roger Desmurs, Francis Pierre
  • Patent number: 5091591
    Abstract: A process comprising the addition of a degradation inhibiting effective amount of an ammonium, alkali metal, alkaline earth metal or transition metal of oxidation number +2 salt of an aliphatic mono or dicarboxylic acid to a composition comprising a phenol and a bisphenol, the addition occurring prior to a procedure which subjects the bisphenol to substantial heat, said bisphenol produced from an acidic ion exchange resin catalyzed reaction of a phenol and a ketone or aldehyde.
    Type: Grant
    Filed: November 13, 1990
    Date of Patent: February 25, 1992
    Assignee: General Electric Company
    Inventor: Michael J. Cipullo
  • Patent number: 5087767
    Abstract: A method for preparing 2,2-bis(4-hydroxyphenyl)propane comprises reacting acetone and phenol in the presence of an acidic ion-exchange resin as a catalyst wherein the reaction of acetone and phenol is performed while removing a part of the water generated during the reaction from a mixed solution containing acetone and phenol by a pervaporation method. According to the method, the water generated through the reaction can rapidly be removed simultaneously with or alternatively to the reaction by a pervaporation operation and, therefore, the catalytic activity of the ion-exchange resin is not impaired at all. Moreover, any complicated operations associated with the dehydration are not required. Thus, the acidic ion-exchange resin catalyst can continuously be used over a long time period without any treatment for the regeneration thereof. Further, according to the method, bisphenol A can be economically prepared from acetone and phenol in a high conversion rate and high yield.
    Type: Grant
    Filed: December 20, 1990
    Date of Patent: February 11, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Kenichi Okamoto, Hidetoshi Kita, Yasuo Tanaka, Shigeru Iimuro
  • Patent number: 5075511
    Abstract: Bisphenol-A is prepared by reacting an excess of phenol with acetone in the presence of a modified sulfonic acid cationic exchange resin catalyst having a plurality of sulfonic acid sites of the general formula ##STR1## in which IER represents the ionic exchange resin backbone, each a and b is an integer from 0 to about 5, and each R is selected independently from H, OH, SH and alkyl groups. The catalyst exhibits high activity and selectivity at moderate reaction temperatures, low production of colored impurities, and high stability.
    Type: Grant
    Filed: June 19, 1990
    Date of Patent: December 24, 1991
    Assignee: Shell Oil Company
    Inventor: Simon M. Li
  • Patent number: 5059721
    Abstract: In a process for the preparation of a bisphenol by condensation of a phenolic compound and a carbonyl compound in the presence of an acidic ion exchange resin catalyst, strong acids that leach from the acidic ion exchange resin catalyst into the reaction effluent are scavenged by a carbon adsorbent. The acid scavenging improves the product quality and yield by reducing acid catalyzed cracking of bisphenols during purification and finishing steps.
    Type: Grant
    Filed: July 31, 1990
    Date of Patent: October 22, 1991
    Assignee: Shell Oil Company
    Inventors: Joseph B. Powell, Zaida Diaz
  • Patent number: 5034498
    Abstract: A method and apparatus for producing water-soluble resin and a resin product made by that method, the method including the steps of supplying a volume of an acidic pyrolysis oil, raising the pH of the oil above 7.0 to partially polymerize the oil, and heating the partially polymerized oil to encourage further polymerization to form the resin product.
    Type: Grant
    Filed: July 19, 1989
    Date of Patent: July 23, 1991
    Assignee: Biocarbons Corporation
    Inventor: Andrew Himmelblau
  • Patent number: 5019656
    Abstract: A process for preparing p-hydroxybenzyl alcohol or a derivative thereof comprising reacting a phenol and a formaldehyde source under a basic condition is disclosed, wherein the reaction is carried out in an alcoholic organic solvent in the presence of a crown ether. The process achieves high selectivity toward the para position without involving high cost.
    Type: Grant
    Filed: February 27, 1990
    Date of Patent: May 28, 1991
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Hiroshi Iwane, Takahiro Sugawara, Naoki Suzuki
  • Patent number: 5008470
    Abstract: The present disclosure is directed to acid scavenging in the acid-catalyzed preparation of a bisphenol by condensation of a phenolic compound and a carbonyl compound. During the preparation, strong acids leach from the acidic ion exchange resin catalyst into the reaction effluent. These acids can be scavenged effectively and without contamination by an inorganic oxide before purification of the product. The acid scavenging improves the product quality and yield by reducing acid catalyzed cracking of bisphenols during purification and finishing steps.
    Type: Grant
    Filed: November 30, 1989
    Date of Patent: April 16, 1991
    Assignee: Shell Oil Company
    Inventors: Joseph B. Powell, Christopher W. Uzelmeier