Preparing From A Phenol And An Aldehyde Or Ketone Patents (Class 568/727)
  • Patent number: 5001281
    Abstract: Bis-phenols are isomerized in the presence of an acidic perfluorinated polymer catalyst.
    Type: Grant
    Filed: August 11, 1989
    Date of Patent: March 19, 1991
    Assignee: Shell Oil Company
    Inventor: Simon M. Li
  • Patent number: 4996373
    Abstract: The invention relates to a process for producing dihydroxydiarylalkanes from carbonyl compounds and phenols under high pressure.
    Type: Grant
    Filed: October 10, 1989
    Date of Patent: February 26, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ludwig Bottenbruch, Heinrich Ruppert, Neil S. Isaacs, Kenneth G. Latham
  • Patent number: 4990686
    Abstract: Crude 2,2-bis-(3,5-dimethyl-4-hydroxyphenyl)propane (=tetramethyl-bisphenol A=TMBPA) can be purified by recrystallization, if C.sub.1 -C.sub.4 -monoalcohols with a water content of 2 to 40% by weight relative to the total weight of alcohol and water are used in an amount of 70 to 250% by weight, relative to the amount of TMBPA and the recrystallization is carried out at a temperature of 65.degree. to 150.degree. C.
    Type: Grant
    Filed: December 27, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Rauchschwalbe, Heinz-Ulrich Blank, Volkmar Handschuh
  • Patent number: 4982014
    Abstract: Dihydroxydiphenyl cycloalkanes corresponding to the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent hydrogen, halogen, C.sub.1 -C.sub.8 alkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.6 -C.sub.10 aryl and C.sub.7 -C.sub.12 aralkyl,m is an integer of from 4 to 7,R.sup.3 and R.sup.4, individually selectable for each X, independently of one another represent hydrogen or C.sub.1 -C.sub.6 alkylandX represents carbonwith the proviso that, at at least one atom X, both R.sup.3 and R.sup.4 are alkyl, a process for their production, their use for the production of high molecular weight polycarbonates, the polycarbonates made from dihydroxydiphenyl cycloalkane of formula (I) and films made from these polycarbonates.
    Type: Grant
    Filed: August 4, 1989
    Date of Patent: January 1, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Freitag, Uwe Westeppe, Claus H. Wulff, Karl-Herbert Fritsch, Carl Casser, Gunther Weymans, Lutz Schrader, Werner Waldenrath
  • Patent number: 4962240
    Abstract: A method for symmetrically dimerizing phenols which comprises oxidizing phenols in molten state in the liquid phase using a transition metal compound as a catalyst and an oxygen-containing gas as an oxidizing agent to conduct dimerization; and a process for producing diphenols which comprises oxidizing phenols in molten state in the liquid phase using a transition metal compound as a catalyst and an oxygen-containing gas as an oxidizing agent to conduct dimerization, and then interrupting introduction of the oxygen-containing gas to conduct a proton disproportionation reaction.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: October 9, 1990
    Assignee: Danippon Ink and Chemicals, Inc.
    Inventors: Taku Kitamura, Noriko Kurokawa, Katsuji Takahashi
  • Patent number: 4954661
    Abstract: A method for preparing high-purity bisphenol A which comprises a principal process comprising a first reaction step for reacting phenol with acetone, a first concentration adjusting step, a first crystallization step for precipitating crystals of the adduct of bisphenol A with phenol, a first separation step for separating a solution containing the crystals of the adduct into the crystals and the mother liquor and a phenol removing step for removing phenol from the crystals of the adduct; and a sub-process comprising a second reaction step for reacting p-isopropenylphenol with phenol, a second concentration adjusting step, a second crystallization step, a second separation step for separating a solution containing the second any crystals of the adduct into the second any crystals and the second mother liquor and a cleaving step, the first mother liquor from the principal process being fed to the sub-process and the second any crystals of the adduct from the sub-process being fed to the principal process, is h
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: September 4, 1990
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shigeru Iimuro, Yoshio Morimoto, Takashi Kitamura
  • Patent number: 4950804
    Abstract: A process for producing high-purity bisphenol A comprises reacting phenol with acetone in the presence of hydrochloric acid as the catalyst to obtain a product mixture, removing the hydrochloric acid from the product mixture, thereby yielding a liquid mixture, adding water to the liquid mixture, evaporating a water-phenol mixture from the liquid mixture under reduced pressure, thereby cooling the liquid mixture and crystallizing out the adduct of bisphenol A with phenol, and finally recovering bisphenol A from the adduct, wherein an improvement comprises treating the water-phenol mixture with a weakly basic ion-exchange resin and recycling and reusing the treated mixture as the water to be added to the liquid mixture. This process does not causes any troubles such as the corrosion of equipment and the decomposition and discoloration of bisphenol A during distillation.
    Type: Grant
    Filed: February 14, 1989
    Date of Patent: August 21, 1990
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shigeru Iimuro, Yoshio Morimoto, Takashi Kitamura
  • Patent number: 4950807
    Abstract: A process for producing high-purity bisphenol A comprises reacting phenol with acetone in the presence of an acid catalyst to obtain a product mixture, removing the acid catalyst from the product mixture, thereby yielding a liquid mixture, treating the liquid mixture with a weakly basic ion-exchange resin having pyridyl groups as the exchange groups, and purifying the treated liquid mixture. The process does not cause any corrosion of equipment and any decomposition and discoloration of bisphenol A during distillation.
    Type: Grant
    Filed: February 10, 1989
    Date of Patent: August 21, 1990
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shigeru Iimuro, Yoshio Morimoto, Takashi Kitamura
  • Patent number: 4950806
    Abstract: A process for crystallizing the adduct of bisphenol A with phenol from a phenol solution in the presence of water comprises controlling the concentration of bisphenol A in said solution by removing portion of the phenol from said solution or adding phenol to said solution according to feedback control based on the measurement of solution density to obtain an adjusted solution, and feeding the adjusted solution to the crystallizer in which its inside wall is kept at a temperature higher than that of the adjusted solution, provided the temperature difference being smaller than 5.degree. C. The crystallized adduct has a uniform particle size and a high purity.
    Type: Grant
    Filed: February 17, 1989
    Date of Patent: August 21, 1990
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shigeru Iimuro, Yoshio Morimoto, Takashi Kitamura
  • Patent number: 4946877
    Abstract: In a process for producing bisphenol A by reacting phenol and acetone in the presence of hydrochloric acid as a catalyst, the improvement comprising adding the water-containing phenol separated from the reaction product mixture in the purification stage to the reaction mixture containing phenol and acetone, in such an amount that the water content in the reaction mixture is within the range of 1 to 5 wt%, said water-containing phenol being obtained from the dehydrochlorination step of the reaction product mixture, condensing the distilled off gases and liquid-separating of the condensates.
    Type: Grant
    Filed: February 7, 1989
    Date of Patent: August 7, 1990
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shigeru Imuro, Yoshio Morimoto, Takashi Kitamura
  • Patent number: 4942265
    Abstract: The process for preparing 2,2-bis(4-hydroxyphenyl)propane (bisphenol A) by reacting acetone with phenol and decomposing the resultant adduct of bisphenol A and phenol is well known. However, the quality of bisphenol A thus obtained is not always satisfactory.In the process of this invention, the adduct is washed with phenol recovered by decomposing an adduct of bisphenol A and phenol, and then bisphenol A is prepared by decomposing the washed adduct.The bisphenol A prepared by the process of this invention has an extremely high quality and is suitable for the preparation of polycarbonate used for optical parts.
    Type: Grant
    Filed: November 28, 1988
    Date of Patent: July 17, 1990
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shigeru Iimuro, Takashi Kitamura, Yoshio Morimoto
  • Patent number: 4937392
    Abstract: A process for preparing 4,4'-dihydroxydiphenylmethane, which comprises reacting phenol with formaldehyde in the presence of an acidic catalyst and separating the aimed 4,4'-dihydroxydiphenylmethane from the crude dihydroxydiphenylmethane thus obtained, is disclosed. According to this process, 4,4'-dihydroxydiphenylmethane can be separated from its isomers and oligomers at a high purity and at a high yield, compared with those achieved by known methods. Thus highly useful 4,4'-dihydroxydiphenylmethane can be advantageously prepared on an industrial scale.
    Type: Grant
    Filed: March 2, 1989
    Date of Patent: June 26, 1990
    Assignee: Mitsubishi Petrochemical Company, Ltd.
    Inventors: Makoto Imanari, Hiroshi Iwane, Takahiro Sugawara, Satoshi Ohtaka, Naoki Suzuki
  • Patent number: 4935553
    Abstract: A process for preparing high purity bisphenol A comprising feeding continuously phenol and acetone in the presence of a hydrochloric acid catalyst into a first stage reactor and reacting phenol and acetone in the range of 20-60 mol % of acetone conversion and continuously removing the first reaction product from the first stage reactor. The first reaction product is fed into a second stage reactor and the reaction of phenol and acetone is completed to obtain a second reaction product from which bisphenol A is recovered.
    Type: Grant
    Filed: January 6, 1989
    Date of Patent: June 19, 1990
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shigeru Iimuro, Yoshio Morimoto, Takashi Kitamura
  • Patent number: 4931594
    Abstract: A method for making aromatic bisphenols such as 9,9-bis-(4-hydroxyphenyl)fluorene by reacting an aromatic ketone, for example a diaryl ketone or diaryl diketone, with a phenol in the present of an insoluble strongly acidic cationic ion exchange resin as an acidic condensation catalyst, which latter may be used in the presence of a co-catalyst containing sulfur.
    Type: Grant
    Filed: October 26, 1988
    Date of Patent: June 5, 1990
    Assignee: Rohm GmbH
    Inventors: Joachim Knebel, Volker Kerscher, Werner Ude
  • Patent number: 4918245
    Abstract: This invention is a process for the preparation of bisphenol A from acetone and phenol. By this invention, the formation of by-products is extremely decreased and post treatment steps can be simplified.This invention involves the following steps. (1) One mole of acetone is reacted with 4 to 12 moles of phenol in the presence of a sulfonic acid type cation exchange resin catalyst modified with a mercapto group-containing compound such as mercaptoethylamine to convert 20 to 60% of acetone, and (2) the reaction mixture containing unreacted acetone is successively reacted to the presence of the hydrochloric acid catalyst.The formation of by-products such as 2-(2-hydroxyphenyl)-2-(4-hydroxyphenyl)propane, Dianin's compound and the like is remarkably reduced by the process of this invention.
    Type: Grant
    Filed: November 28, 1988
    Date of Patent: April 17, 1990
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shigeru Iimuro, Takashi Kitamura, Yoshio Morimoto
  • Patent number: 4912263
    Abstract: This invention relates to an ionic exchanger modified with thiazolines, to its preparation and to its use for the preparation of condensation products, particularly bisphenols.
    Type: Grant
    Filed: August 9, 1988
    Date of Patent: March 27, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Rudolph, Claus Wulff, Jurgen Hinz, Norbert Bachem
  • Patent number: 4906789
    Abstract: A process for the production of bisphenol A from phenol and acetone, comprises introducing a substantially anhydrous reaction mixture of phenol, acetone, and recycled solution of bisphenol A and reaction by-products in phenol into a reaction zone containing a cation-exchange resin catalyst, such catalyst being a mixture of resin having a macroporous structure and resin having a microporous structure in a ratio of 0.05:1 to 0.5:1 by weight, the mol ratio of phenol to acetone being 5:1 to 30:1, and the concentration of bisphenol A being 12 to 20% by weight. The temperature of the reaction zone is maintained between 60 degrees and 95 degrees C. The resulting reacted reaction mixture is withdrawn from the reaction zone, the concentration of bisphenol A being 21 to 35% by weight and the amount of reaction by-products being 12 to 24% by weight. Such withdrawn reaction mixture is treated to recover bisphenol A product and to provide the recycled solution of bisphenol A and reaction by-products in phenol.
    Type: Grant
    Filed: September 28, 1988
    Date of Patent: March 6, 1990
    Assignees: Instytut Ciezkiej Syntezy Organicznej "Blachownia", Zaklady Chemiczne "Blachownia"
    Inventors: Edward Grzywa, Maciej Kiedik, Jo Kolt, Adam Mazur, Jerzy Marszycki, Eugeniusz Zajac, Anna Rzodeczko, Jerzy Czyz, Kazimierz Terelak, Zbigniew Swiderski, Teodor Bek
  • Patent number: 4895988
    Abstract: The mutual condensation of aromatic and carbonylic compounds is carried out with zeolitic materials derived from silicalite by replacing a portion of silicon with B and Al, Al and Ti, Ti and Fe, and with ZSM-5, to yield diaryl-alkanes.
    Type: Grant
    Filed: October 20, 1987
    Date of Patent: January 23, 1990
    Assignees: Eniricerche S.p.A., Enichem Sythesis S.p.A., Snamprogetti S.p.A.
    Inventors: Mario G. Clerici, Giuseppe Bellussi
  • Patent number: 4876395
    Abstract: A process which comprises(a) contacting an excess of a phenol with a ketone in the presence of an acidic ion exchange resin catalyst;(b) recovering thereafter a stream from an acidic ion exchange resin catalyst, said stream including the dihydric phenol, unreacted phenol, isomers of the desired dihydric phenol and acid impurities derived from the acidic ion exchange resin catalyst;(c) removing a major portion of the desired dihydric phenol from the stream of (b);(d) adding to the dihydric phenol effective quantities of a Group II-a metal or transition metal of oxidation number +2 carbonate to color stablize the dihydric phenol;(e) recovering the solid dihydric phenol and the metal carbonate.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: October 24, 1989
    Assignee: General Electric Company
    Inventor: Gaylord M. Kissinger
  • Patent number: 4876391
    Abstract: A process which comprises(a) contacting an excess of a phenol with a ketone in the presence of an acidic ion exchange resin catalyst;(b) recovering thereafter a stream from the acidic ion exchange resin catalyst including the dihydric phenol, unreacted phenol, isomers of the desired dihydric phenol and acid impurities derived from the acidic ion exchange resin catalyst;(c) removing a major portion of the desired dihydric phenol from the stream of (b);(d) separating the stream including phenol, a small portion of the desired dihydric phenol, isomers of the desired dihydric phenol, and acidic impurities derived from the acidic ion exchange resin catalyst into a major stream and a minor stream by volume;(e) introducing into the minor stream created at step (d) sufficient quantities of a tetraorganoammonium borohydride to effectively neutralize the acidic impurities derived from the acidic ion exchange resin catalyst; and(f) recovering from the minor stream desirable dihydric phenol.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: October 24, 1989
    Assignee: General Electric Company
    Inventor: Gaylord M. Kissinger
  • Patent number: 4859803
    Abstract: A process for the preparation of bisphenols which comprises treating a phenol with a ketone in the presence of a cation exchange resin catalyst and a mercaptan co-catalyst in a reactor or a series of reactors wherein all of the phenol and a portion of the mercaptan is injected into the beginning of the reactor or the first reactor and the remaining mercaptan is injected along the reactor length or in the subsequent reactors whereby cyclic dimers formation is reduced.
    Type: Grant
    Filed: May 16, 1988
    Date of Patent: August 22, 1989
    Assignee: Shell Oil Company
    Inventor: Paul V. Shaw
  • Patent number: 4847433
    Abstract: A process which comprises(a) contacting an excess of a phenol with a ketone in the presence of an acidic ion exchange resin catalyst;(b) recovering thereafter a stream from the acidic ion exchange resin catalyst including the dihydric phenol, unreacted phenol, isomers of the desired dihydric phenol and acid impurities derived from the acidic ion exchange resin catalyst;(c) removing a major portion of the desired dihydric phenol from the stream of (b);(d) separating the stream including phenol, a small portion of the desired dihydric phenol, isomers of the desired dihydric phenol, and acidic impurities derived from the acidic ion exchange resin catalyst into a major stream and a minor stream by volume;(e) recycling the major stream so as to contact the acidic ion exchange resin catalyst of (a) together with new phenol and ketone so as to maintain a balance between the color of the final desired dihydric phenol product and impurities found therein;(f) recovering from the small stream desireable dihydric phenol,
    Type: Grant
    Filed: May 23, 1988
    Date of Patent: July 11, 1989
    Assignee: General Electric Company
    Inventor: Gaylord M. Kissinger
  • Patent number: 4847432
    Abstract: A method for treating a sulfonic acid-containing ion exchange resin to remove destabilizing impurities therefrom is disclosed. The method comprises contacting the resin with a base, followed by contact with a strong acid. The treated ion exchange resin is particularly suitable for use as a catalyst in the preparation of bisphenol A.
    Type: Grant
    Filed: December 28, 1987
    Date of Patent: July 11, 1989
    Assignee: General Electric Company
    Inventor: Gary R. Faler
  • Patent number: 4825010
    Abstract: By-products of bis-phenol synthesis are isomerized in the presence of a mercapto modified cation exchange resin catalyst.
    Type: Grant
    Filed: October 19, 1987
    Date of Patent: April 25, 1989
    Assignee: Shell Oil Company
    Inventor: Simon M. Li
  • Patent number: 4822923
    Abstract: By-products of bis-phenol synthesis are isomerized in the presence of an acid catalyst and a free mercaptan co-catalyst.
    Type: Grant
    Filed: October 19, 1987
    Date of Patent: April 18, 1989
    Assignee: Shell Oil Company
    Inventor: Simon M. Li
  • Patent number: 4777301
    Abstract: An aldehyde or ketone is condensed with an aromatic compound by contacting the aldehyde or ketone and the aromatic compound with a non-zeolitic molecular sieve, which has in its calcined form an adsorption of isobutane of at least about 2 percent by weight of the non-zeolitic molecular sieve at a partial pressure of 500 torr and a temperature of 20.degree. C. Among the condensations which can be effected is the condensation of acetone with phenol to produce bisphenol A.
    Type: Grant
    Filed: June 25, 1986
    Date of Patent: October 11, 1988
    Assignee: Union Carbide Corporation
    Inventor: Kurt D. Olson
  • Patent number: 4769501
    Abstract: There is disclosed a process for producing an alkylphenol comprising reacting a phenol with an aldehyde and hydrogen in the presence of (a) an alkaline or alkaline earth metal catalyst selected from a hydroxide of an alkaline metal, hydroxide of an alkaline earth metal, a carbonate of an alkaline metal, and a hydrogencarbonate of an alkaline metal and (b) a hydrogenation catalyst. By the use of the process, the alkylphenols can be produced in good yield in one stage method.
    Type: Grant
    Filed: July 21, 1987
    Date of Patent: September 6, 1988
    Assignee: Idemitsu Petrochemical Co., Ltd.
    Inventor: Masahiro Iwahara
  • Patent number: 4766255
    Abstract: A process for the preparation of gem-bis(hydroxyaryl)alkanes which comprises the reaction of a ketone, a hydroxyarene and an alkylhalosilane.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: August 23, 1988
    Assignee: Xerox Corporation
    Inventors: Beng S. Ong, Lupu Alexandru
  • Patent number: 4740634
    Abstract: A process for crystallizing bisphenol-A which comprises:a. adding water to a mixture comprising bisphenol-A, about 0.5 to 15 weight percent of diphenol isomers and impurities, said mixture essentially free of phenol,b. maintaining the combined water and said mixture of (a) at a temperature sufficient to melt the solid material of step (a),c. adiabatically cooling the water and said mixture to below about 90.degree. C.,d. separating crystallized bisphenol-A from the mother liquor, ande. washing the crystallized bisphenol-A with an organic solvent which is at least substantially insoluble in water.
    Type: Grant
    Filed: October 20, 1986
    Date of Patent: April 26, 1988
    Assignee: General Electric Company
    Inventors: Isabel M. Gomes de Matos, Gaylord M. Kissinger
  • Patent number: 4740635
    Abstract: A process for crystallizing bisphenol-A which comprises:a. adding water to a mixture comprising bisphenol-A, about 0.5 to 15 weight percent of diphenol isomers and impurities, said mixture essentially free of phenol,b. maintaining the combined water and said mixture of (a) at a temperature sufficient to melt the solid material of step (a),c. adiabatically cooling the water and said mixture to below about 90.degree. C., andd. separating crystalline bisphenol-A from the mother liquor.
    Type: Grant
    Filed: October 20, 1986
    Date of Patent: April 26, 1988
    Assignee: General Electric Company
    Inventors: Isabel M. Gomes de Matos, Gaylord M. Kissinger
  • Patent number: 4694111
    Abstract: The production of a 1-hydroxy-2-lower alkoxyalkyl benzene, e.g. 2-(1'-methoxyethyl) phenol, is carried out by reacting phenol with a lower acetal or ketal, e.g., 1,1-dimethoxyethane at an elevated temperature in the presence of an H-ZSM-5 zeolite, as catalyst.
    Type: Grant
    Filed: July 9, 1986
    Date of Patent: September 15, 1987
    Assignee: Celanese Corporation
    Inventor: Balaram B. G. Gupta
  • Patent number: 4692555
    Abstract: A process for the production of diphenolic compounds having a divalent bridge. A first disubstituted phenol is reacted with an aldehyde in the presence of a secondary amine and excess alcohol to form an ether intermediate. The ether intermediate is reacted with a phenol having an open ortho or para position to form a diphenolic.
    Type: Grant
    Filed: April 9, 1984
    Date of Patent: September 8, 1987
    Assignee: Ethyl Corporation
    Inventor: Kju H. Shin
  • Patent number: 4683345
    Abstract: Process of preparation of a bisphenol by the condensation of a phenol carrying a halogen substituent and alkyl groups with an aldehyde in a solvent for the phenol, in the presence of sulphuric acid; the proportion of acid with respect to the phenol is such that after the condensation and absorption by the acid of the water eliminated, the acid contains less than 50% of water by weight.
    Type: Grant
    Filed: April 16, 1986
    Date of Patent: July 28, 1987
    Assignee: Colette Nouvel
    Inventor: Guy Lejeune
  • Patent number: 4675458
    Abstract: A method for making 9,9-bis-(4-hydroxyphenyl)-fluorene by reacting fluorenone with phenol at a temperature from 20.degree. to 100.degree. C. in the presence of sulfuric acid of a concentration higher than 70 percent and of a mercaptan, and particularly beta-mercaptopropionic acid, as acidic condensing agents.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: June 23, 1987
    Assignee: Ronm GmbH
    Inventors: Achim Riemann, Werner Ude
  • Patent number: 4590303
    Abstract: A method of making bisphenol A from phenol and acetone is provided which allows for the use of reactor acetone feed in the rearrangement reactor. As a result, improved acetone conversion is realized and BPA productivity is enhanced.
    Type: Grant
    Filed: June 3, 1985
    Date of Patent: May 20, 1986
    Assignee: General Electric Company
    Inventor: Ashok K. Mendiratta
  • Patent number: 4584416
    Abstract: A sulfonated aromatic organic polymer, such as sulfonated polystyrene ion-exchange resin is provided having ionically bound N-alkylaminoorganomercaptan groups. The ion-exchange resin can be used to effect phenol-ketone condensation.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: April 22, 1986
    Assignee: General Electric Company
    Inventors: Eric J. Pressman, Paul R. Willey
  • Patent number: 4564691
    Abstract: A process is provided for preparing a substituted 2,3-dihydrobenzofuran of the general formula ##STR1## in which R.sub.a is hydrogen, halogen, alkyl, straight or branched having from 1 to 4 carbon atoms, aryl, alkaryl, --OH, --OR.sub.3, --N(R.sub.d).sub.2, where R.sub.3 and R.sub.d are alkyl, straight or branched having from 1 to 4 carbon atoms; R.sub.b is alkyl, straight or branched, having from 1 to 6 carbon atoms, aryl, alkaryl; and R.sub.c is hydrogen or the same as R.sub.b, by the rearrangement of a 1,1-bis(2-hydroxybenzene) alkyl and/or aryl-ethane, in the presence of catalytic amounts of a mineral acid or organic acid such as phosphoric, sulfuric or p-toluenesulfonic, at elevated temperatures from 180.degree. to 250.degree. C., and withdrawing the resulting products from the reaction mixture as they are formed. The starting 1,1-bis(2-hydroxybenzene) alkyl and/or aryl-ethane compounds may be obtained by the catalyzed reaction of a substituted biphenol with an aldehyde.
    Type: Grant
    Filed: April 19, 1984
    Date of Patent: January 14, 1986
    Assignee: Enichimica Secondaria S.p.A.
    Inventors: Carlo Neri, Villiam Giroldini, Antonio Rinaldi, Mario Traversoni, Mario Clerici
  • Patent number: 4562266
    Abstract: Process for the preparation of 2,3-dihydro-2,2-dimethyl-7-benzofuranol, comprising the reaction between catechol or 4-tert.butyl catechol and isobutyraldehyde in the presence of catalytic amounts of at least one compound selected from the group consisting of the oxides, hydroxides, alcoholates and carboxylates of metals belonging to the Groups IA, IIA, IIB and VIIB of the Periodic System of the Elements and the subsequent reaction of rearrangement of the products which have been obtained, optionally previously removing one or more low-boiling components, in the presence of a compound having acidic properties, of an organic or a mineral nature. The product is useful in the synthesis of pesticides.
    Type: Grant
    Filed: April 19, 1984
    Date of Patent: December 31, 1985
    Assignee: Enichimica Secondaria, S.p.A.
    Inventors: Carlo Neri, Villiam Giroldini, Mario Traversoni, Guido Guizzi, Emilio Perrotti, Antonio Rinaldi
  • Patent number: 4535191
    Abstract: Novel polycarbonates are provided which exhibit rubbery and elastomeric properties which are the polymerized reaction products of:(i) a carbonate precursor; and(ii) at least one dihydric phenol represented by the general formula ##STR1## wherein R is selected from straight chain alkyl radicals containing from 8 to about 30 carbon atoms;each R.sup.1 is independently selected from halogen monovalent hydrocarbon, and monovalent hydrocarbonoxy radicals;each R.sup.2 is independently selected from halogen, monovalent hydrocarbon, and monovalent hydrocarbonoxy radicals; andn and n' are independently selected from whole numbers having a value of from 0 to 4 inclusive.
    Type: Grant
    Filed: February 23, 1984
    Date of Patent: August 13, 1985
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles V. Hedges
  • Patent number: 4508886
    Abstract: A method is described for making adhesive from biomass. A liquefaction oil is prepared from lignin-bearing plant material and a phenolic fraction is extracted therefrom. The phenolic fraction is reacted with formaldehyde to yield a phenol-formaldehyde resin.
    Type: Grant
    Filed: March 30, 1984
    Date of Patent: April 2, 1985
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Janet A. Russell, William F. Riemath
  • Patent number: 4503266
    Abstract: In a process for the preparation of phenol-aromatic ketone condensation products by reaction of phenols and ketones in the presence of a gaseous hydrogen halide, the improvement comprising adding in catalytic amounts up to less than molar amounts based on the ketone as an additional condensation agent at least one bivalent, trivalent or tetravalent metal halide, introducing the gaseous hydrogen halide and after termination of the condensation reaction, adding water to the reaction mixture and recovering the purified condensation product and to the novel monomers of 9,9-bis-(4-hydroxyphenyl)-fluorene with a melting point of at least 226.degree. C. and 1,1-bis-(4-hydroxyphenyl)-1-phenylethene with a melting point of at least 189.degree. C. which are useful for the preparation of improved polyester resins.
    Type: Grant
    Filed: June 7, 1984
    Date of Patent: March 5, 1985
    Assignee: Isovolta Osterreichische Isolierstoffwerke Aktiengesellschaft
    Inventor: Otto Szabolcs
  • Patent number: 4467121
    Abstract: Fluorinated bisphenols having a fluorinated alkyl group and a hydrogen atom upon the methylene carbon atom are prepared at atmospheric pressure or at low pressures from a phenol reactant and a fluorinated aldehyde compound in the presence of gaseous hydrogen chloride or gaseous hydrogen bromide catalyst. The fluorinated bisphenols having the fluorinated alkyl group and a hydrogen atom upon the methylene carbon atom are produced in excellent yields and are used for making flame-retardant polycarbonates and polyester-carbonate copolymers.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: August 21, 1984
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles V. Hedges
  • Patent number: 4467122
    Abstract: In a process for the preparation of phenol-aromatic ketone condensation products by reaction of phenols and ketones in the presence of a gaseous hydrogen halide, the improvement comprising adding in catalytic amounts up to less than molar amounts based on the ketone as an additional condensation agent at least one bivalent, trivalent or tetravalent metal halide, introducing the gaseous hydrogen halide and after termination of the condensation reaction, adding water to the reaction mixture and recovering the purified condensation product and to the novel monomers of 9,9-bis-(4-hydroxyphenyl)-fluorene with a melting point of at least 226.degree. C. and 1,1-bis-(4-hydroxyphenyl)-1-phenylethene with melting point of at least 189.degree. C. which are useful for the preparation of improved polyester resins.
    Type: Grant
    Filed: May 18, 1982
    Date of Patent: August 21, 1984
    Assignee: Isovolta Osterreichische Isolierstoffwerke Aktiengesellschaft
    Inventor: Otto Szabolcs
  • Patent number: 4460799
    Abstract: This invention relates to a process for the selective preparation of ortho-hydroxybenzyl alcohols and, in particular, ortho-hydroxybenzyl alcohol. According to the invention, the reaction of a phenol with an aldehyde in an initially anhydrous medium and in the presence of a catalytic amount of a metal phenate, results in the selective production of ortho-hydroxybenzyl alcohols.
    Type: Grant
    Filed: June 23, 1982
    Date of Patent: July 17, 1984
    Assignee: Isover Saint-Gobain
    Inventors: Robert Perrin, Roger Fugier
  • Patent number: 4446039
    Abstract: Compositions useful as additives for fuels and lubricants can be made by reacting (A) an aromatic compound having an OH or SH group attached to an aromatic nucleus and an aromatic hydrogen atom (e.g., a substituted phenol wherein the substituent is an alkyl group of at least 50 carbon atoms); (B) an aldehyde or reactive equivalent thereof (e.g., formaldehyde); (C) a non-amino hydrogen, active hydrogen compound (e.g., a phenol, N,N-dimethyl aniline, etc.) and optionally, (D) an aliphatic alkylating agent of at least 30 carbon atoms (e.g., a polyisobutene of about 50 carbon atoms).
    Type: Grant
    Filed: May 13, 1981
    Date of Patent: May 1, 1984
    Assignee: The Lubrizol Corporation
    Inventors: John F. Pindar, Jerome M. Cohen
  • Patent number: 4443635
    Abstract: In the production of bisphenols, color bodies which have been adsorbed on cationic exchange resins are removed by washing with at least one phenate selected from phenates of an alkali metal and of ammonia.
    Type: Grant
    Filed: December 6, 1982
    Date of Patent: April 17, 1984
    Assignee: Shell Oil Company
    Inventor: William A. McLaughlin
  • Patent number: 4423252
    Abstract: Bisphenols are prepared by condensation of a phenol with a ketone in the presence of a sulfonic acid type cation exchange resin partially modified with a pyridinealkanethiol of the formula:Py--(CH.sub.2).sub.n SHwherein n is a positive integer and Py is 3-pyridyl when n is 1, or 2-, 3- or 4-pyridyl when n is more than 1.
    Type: Grant
    Filed: July 2, 1981
    Date of Patent: December 27, 1983
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Takao Maki, Tetsuo Masuyama, Toshiharu Yokoyama, Yoshiko Fujiyama
  • Patent number: 4400555
    Abstract: An improved bis-phenol synthesis reactor system is provided using multiple acetone injection in an ion exchange catalyzed BPA synthesis process. This process results in an improved reactant effluent product distribution and color.
    Type: Grant
    Filed: October 6, 1981
    Date of Patent: August 23, 1983
    Assignee: General Electric Company
    Inventor: Ashok K. Mendiratta
  • Patent number: 4400554
    Abstract: Bis(hydroxyphenyl)methanes are prepared by reaction of phenol and formaldehyde in a two-phase mixture containing aqueous phosphoric acid. The reaction conditions can be selected to provide high yields of bis(hydroxyphenyl)methanes or to yield bis(hydroxyphenyl)methanes containing a high concentration of the 4,4'-isomer.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: August 23, 1983
    Assignee: Monsanto Company
    Inventor: Morris R. Ort
  • Patent number: 4391997
    Abstract: An ion exchange catalyzed bisphenol process is described wherein condensation reaction temperature is increased along the path of the reaction which limits the formation of color bodies, tars and other condensation reaction by-product impurities.
    Type: Grant
    Filed: October 23, 1981
    Date of Patent: July 5, 1983
    Assignee: General Electric Company
    Inventor: Ashok K. Mendiratta