Preparing From A Phenol And An Aldehyde Or Ketone Patents (Class 568/727)
-
Patent number: 5516441Abstract: 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: GrantFiled: April 26, 1994Date of Patent: May 14, 1996Assignee: The Lubrizol CorporationInventor: Richard A. Denis
-
Patent number: 5512700Abstract: 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: GrantFiled: March 10, 1995Date of Patent: April 30, 1996Assignee: Dow Deutschland Inc.Inventors: Emil Patrascu, Karl Kraehling, Jochen Gressmann
-
Patent number: 5504251Abstract: 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: GrantFiled: March 9, 1995Date of Patent: April 2, 1996Assignee: General Electric CompanyInventors: Arkady S. Dyckman, Andrey V. Zinenkov, Boris I. Gorovits, Valentina Y. Shefter, John W. Fulmer, William D. Kight
-
Patent number: 5475154Abstract: 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: GrantFiled: March 10, 1994Date of Patent: December 12, 1995Assignee: Rohm and Haas CompanyInventors: Eric G. Lundquist, Michael P. Bigwood
-
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
-
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
-
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
-
Patent number: 5434316Abstract: 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: GrantFiled: July 28, 1994Date of Patent: July 18, 1995Assignee: General Electric CompanyInventor: Gaylord M. Kissinger
-
Patent number: 5428075Abstract: 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: GrantFiled: May 2, 1994Date of Patent: June 27, 1995Assignee: General Electric CompanyInventors: Eric J. Pressman, Sheldon J. Shafer
-
Patent number: 5414151Abstract: 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: GrantFiled: May 2, 1994Date of Patent: May 9, 1995Assignee: General Electric CompanyInventors: Eric J. Pressman, Sheldon J. Shafer
-
Patent number: 5414152Abstract: 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: GrantFiled: May 10, 1994Date of Patent: May 9, 1995Assignee: General Electric CompanyInventor: Michael J. Cipullo
-
Patent number: 5395915Abstract: 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 molecType: GrantFiled: August 12, 1993Date of Patent: March 7, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shigeru Iimuro, Satoru Ito, Tomoko Takashima, Takashi Kitamura
-
Patent number: 5387725Abstract: 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: GrantFiled: July 12, 1993Date of Patent: February 7, 1995Assignee: The Dow Chemical CompanyInventors: 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: 5382712Abstract: 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: GrantFiled: April 18, 1994Date of Patent: January 17, 1995Assignee: Chiyoda CorporationInventors: 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: 5362900Abstract: A method comprising purifying impure bisphenol-A by fractional melt crystallization in a falling film dynamic crystallizer.Type: GrantFiled: August 18, 1993Date of Patent: November 8, 1994Assignees: General Electric Co., Sulzer Canada, Inc.Inventors: Gaylord M. Kissinger, Nicholas P. Wynn
-
Patent number: 5345001Abstract: 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: GrantFiled: August 23, 1993Date of Patent: September 6, 1994Assignee: Rutgerswerke Aktiengesellschaft AGInventors: Stephan Schroter, Achim Hansen, Arno Gardziella, Peter Adolphs
-
Patent number: 5345000Abstract: 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: GrantFiled: March 3, 1993Date of Patent: September 6, 1994Assignee: Chiyoda CorporationInventors: Nobuo Moriya, Keiji Shimoda, Sachio Asaoka, Takao Kameda, Kouji Sakashita, Tetsuo Maejima, Makoto Yasui, Hiroaki Nishijima, Nobuhiro Onda, Takeshi Kouzaki
-
Patent number: 5336813Abstract: 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: GrantFiled: January 29, 1993Date of Patent: August 9, 1994Assignee: General Electric CompanyInventors: Michael J. Cipullo, John W. Fulmer
-
Patent number: 5324867Abstract: 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: GrantFiled: July 13, 1992Date of Patent: June 28, 1994Assignee: Chiyoda CorporationInventors: 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: 5315042Abstract: 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: GrantFiled: March 22, 1993Date of Patent: May 24, 1994Assignee: General Electric CompanyInventors: Michael J. Cipullo, Gaylord M. Kissinger, Isabel M. Matos
-
Patent number: 5304688Abstract: 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: GrantFiled: April 13, 1993Date of Patent: April 19, 1994Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, Muthiah N. Inbasekaran
-
Patent number: 5302774Abstract: 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: GrantFiled: August 9, 1993Date of Patent: April 12, 1994Assignee: Bayer AktiengesellschaftInventors: Klaus Berg, Hans-Josef Buysch, Alfred Eitel, Gerhard Fennhoff, Otto Immel, Ralf Pakull, Bernhard Wehrle, Claus Wulff
-
Patent number: 5300700Abstract: 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: GrantFiled: April 20, 1993Date of Patent: April 5, 1994Assignee: Bayer AktiengesellschaftInventors: Georg Malamet, Hans-Peter Wirges, Claus Wulff, Alfred Eitel
-
Patent number: 5288926Abstract: 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: GrantFiled: February 4, 1993Date of Patent: February 22, 1994Assignee: The Dow Chemical CompanyInventors: Emil Patrascu, Dieter Tank, Jochen Gressmann, Johann-Wilhelm Frey, Ulrich Wallbaum
-
Patent number: 5284981Abstract: This invention relates to a catalyst modified with mercapto amines, its preparation and its use for the preparation of bisphenols.Type: GrantFiled: May 1, 1990Date of Patent: February 8, 1994Assignee: Bayer AktiengesellschaftInventors: Udo Rudolph, Norbert Bachem, Claus Wulff
-
Patent number: 5276213Abstract: 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: GrantFiled: February 10, 1993Date of Patent: January 4, 1994Assignee: Bayer AktiengesellschaftInventors: Volker Serini, Uwe Westeppe, Gerd Fengler, Manfred Hajek, Carl Casser, Helmut Waldmann
-
Patent number: 5248839Abstract: 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: GrantFiled: April 7, 1992Date of Patent: September 28, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shigeru Iimuro, Akira Yamada, Kenichi Ohmura, Toshio Houri, Tsuguo Kawamura
-
Patent number: 5248838Abstract: 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: GrantFiled: January 24, 1992Date of Patent: September 28, 1993Assignee: Minnesota Mining and Manufacturing CompanyInventors: Sergio Massirio, Mauro Besio, Marcello Gagliano, Brunella Fornasari, Angelo Vallarino, Piera Di Mito
-
Patent number: 5233096Abstract: 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: GrantFiled: July 13, 1992Date of Patent: August 3, 1993Assignee: Rohm and Haas CompanyInventor: Eric G. Lundquist
-
Patent number: 5220079Abstract: 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: GrantFiled: April 24, 1992Date of Patent: June 15, 1993Assignee: Mitsubishi Petrochemical Company LimitedInventors: Hiroshi Iwane, Takahiro Sugawara, Naoki Suzuki, Kimiko Kaneko
-
Patent number: 5210329Abstract: 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: GrantFiled: February 18, 1992Date of Patent: May 11, 1993Assignee: General Electric CompanyInventors: Isabel M. Gomes de Matos, Allen Wai-Kee Ko
-
Patent number: 5198591Abstract: 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: GrantFiled: November 22, 1991Date of Patent: March 30, 1993Assignees: 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: 5191128Abstract: 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: GrantFiled: March 12, 1992Date of Patent: March 2, 1993Assignee: Shell Oil CompanyInventor: Simon M. Li
-
Patent number: 5169990Abstract: 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: GrantFiled: February 11, 1992Date of Patent: December 8, 1992Assignee: Rutgerswerke AktiengesellschaftInventors: Winfried Orth, Emmerich Pastorek, Wolfgang Weiss, Hans W. Kleffner
-
Patent number: 5169992Abstract: 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: GrantFiled: April 20, 1992Date of Patent: December 8, 1992Assignee: Texaco Chemical CompanyInventor: John F. Knifton
-
Patent number: 5149886Abstract: 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: GrantFiled: February 11, 1992Date of Patent: September 22, 1992Assignee: Rutgerswerke AGInventors: Winfried Orth, Emmerich Pastorek, Wolfgang Weiss, Hans W. Kleffner
-
Patent number: 5146007Abstract: 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: GrantFiled: June 17, 1991Date of Patent: September 8, 1992Assignee: General Electric CompanyInventor: Michael J. Cipullo
-
Patent number: 5118875Abstract: 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: GrantFiled: October 10, 1990Date of Patent: June 2, 1992Assignee: Exxon Chemical Patents Inc.Inventors: David J. Martella, John J. Jaruzelski, Frank J. Chen
-
Patent number: 5115084Abstract: 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: GrantFiled: January 29, 1991Date of Patent: May 19, 1992Assignee: Biocarbons CorporationInventor: D. Andrew Himmelblau
-
Patent number: 5110994Abstract: 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: GrantFiled: December 10, 1990Date of Patent: May 5, 1992Assignee: ISONOVA Technische Innovationen G.m.b.HInventor: Peter Fialla
-
Patent number: 5107036Abstract: 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: GrantFiled: October 24, 1990Date of Patent: April 21, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Nobuyuki Nakajima, Shuichi Kanagawa, Hideshi Sakamoto, Noriaki Saito, Tadashi Ikushima
-
Patent number: 5105026Abstract: 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: GrantFiled: November 15, 1990Date of Patent: April 14, 1992Assignee: Shell Oil CompanyInventors: Joseph B. Powell, Christopher W. Uzelmeier
-
Patent number: 5105027Abstract: 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: GrantFiled: February 28, 1991Date of Patent: April 14, 1992Assignee: Rhone-Poulenc ChimieInventors: Jean-Roger Desmurs, Francis Pierre
-
Patent number: 5091591Abstract: 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: GrantFiled: November 13, 1990Date of Patent: February 25, 1992Assignee: General Electric CompanyInventor: Michael J. Cipullo
-
Patent number: 5087767Abstract: 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: GrantFiled: December 20, 1990Date of Patent: February 11, 1992Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Kenichi Okamoto, Hidetoshi Kita, Yasuo Tanaka, Shigeru Iimuro
-
Patent number: 5075511Abstract: 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: GrantFiled: June 19, 1990Date of Patent: December 24, 1991Assignee: Shell Oil CompanyInventor: Simon M. Li
-
Patent number: 5059721Abstract: 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: GrantFiled: July 31, 1990Date of Patent: October 22, 1991Assignee: Shell Oil CompanyInventors: Joseph B. Powell, Zaida Diaz
-
Patent number: 5034498Abstract: 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: GrantFiled: July 19, 1989Date of Patent: July 23, 1991Assignee: Biocarbons CorporationInventor: Andrew Himmelblau
-
Patent number: 5019656Abstract: 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: GrantFiled: February 27, 1990Date of Patent: May 28, 1991Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Hiroshi Iwane, Takahiro Sugawara, Naoki Suzuki
-
Patent number: 5008470Abstract: 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: GrantFiled: November 30, 1989Date of Patent: April 16, 1991Assignee: Shell Oil CompanyInventors: Joseph B. Powell, Christopher W. Uzelmeier