Purification Or Recovery Patents (Class 568/749)
  • 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: 5502259
    Abstract: The invention relates to a method for purification of phenol and specifically to a method for purification of phenol produced within the process of joint phenol and acetone production by cumene method.The aim of the invention is to develop a catalyst which has high activity for phenol purification from organic mico-impurities with regeneration of the catalyst and which has high mechanical strength and stability with long catalyst life.This result is obtained by phenol purification using a heterogeneous zeolite catalyst. The acidity of the catalyst measured by butane cracking (K.sub.A) is more than 10.It is preferable to use zeolites which are designated according to the classification of the International Zeolite Association by indices FAU (zeolites X, Y), MFI (for example, ZSM-5), MOR (mordenite), MAZ (omega), BEA (beta), FER (ferrierite) and others. These zeolites can be used with binders (aluminum oxide, silica gel, aluminosilicates or aluminophosphates) and without them.
    Type: Grant
    Filed: August 15, 1994
    Date of Patent: March 26, 1996
    Assignees: General Electric Company, U.S.A., Illa International
    Inventors: Vladimir M. Zakoshansky, Irina I. Vasilieva, Andrei K. Griaznov
  • Patent number: 5491268
    Abstract: A process for purifying phenol, phenol-type compounds, and substituted phenol and phenol-type compounds of contamination by components more acidic than the phenol component comprising treating a phenol containing process stream by contacting the stream with an amphoteric porous inorganic oxide.
    Type: Grant
    Filed: September 23, 1994
    Date of Patent: February 13, 1996
    Assignee: General Electric Company
    Inventor: Michael J. Cipullo
  • Patent number: 5487816
    Abstract: A process to separate in a fractionation zone an admixture comprising phenol, alpha-methylstyrene and water to produce an alpha-methylstyrene stream containing a minimum of phenol. The pH of the overhead aqueous phase is adjusted with a base to greater than about 6.
    Type: Grant
    Filed: June 24, 1994
    Date of Patent: January 30, 1996
    Assignee: UOP
    Inventors: Russell C. Schulz, Constante P. Tagamolila, Patrick J. Bullen
  • Patent number: 5476973
    Abstract: Disclosed herein are a stable m-vinylphenol composition comprising m-vinylphenol and tolylene-2,4-diamine and/or N,N-dimethyl-p-phenylenediamine added thereto, a method of stabilizing m-vinylphenol, which comprises adding tolylene-2,4-diamine and/or N,N-dimethyl-p-phenylenediamine to m-vinylphenol, and a method of purifying m-vinylphenol by distillation, which comprises adding tolylene-2,4-diamine and/or N,N-dimethyl-p-phenylenediamine to m-vinylphenol upon the purification of m-vinylphenol by distillation.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: December 19, 1995
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Rika Hatano, Tadashi Matsumoto, Teruki Matsukami
  • Patent number: 5457244
    Abstract: An improved phenol tar cracking process using a rectification column as a hydrocracker obtains an increased yield of valuable products, phenol, cumene and alpha-methylstyrene, by taking from 50 to 100% of the acetophenone in the reactor overhead with the cracked product stream.
    Type: Grant
    Filed: October 4, 1994
    Date of Patent: October 10, 1995
    Assignee: General Electric Company
    Inventors: Arkadys S. Dyckman, John Fulmer, William D. Kight, Andrey Zinenkov, Vadim P. Boyarsky, Boris I. Gorovits, Leontii M. Krasnov, Alexander S. Malinovski, Yury I. Petrov, Anatoly D. Sorokin, Sergey N. Chernukhin
  • Patent number: 5457246
    Abstract: A process and arrangement for separating and recovering polyol production wastes, including polyol, potassium or sodium phosphate and magnesium silicates, is disclosed. According to the invention, the polyol product waste and caustic salt are combined in a vessel, emulsified and then deemulsified. This causes the contents of the vessel to stratify into three layers. A first stream containing primarily magnesium silicates and a minor amount of caustic salt solution is withdrawn from the vessel and then waterwashed. The water-washed magnesium silicates are then dehydrated and desiccated to obtain commercial grade magnesium silicates. The minor amount of caustic salt solution is dehydrated, crystallized and then desiccated to yield commercial grade anhydrous potassium or sodium phosphate. A second stream containing predominantly polyol oil is withdrawn from the vessel and subsequently filtered and dehydrated to obtain commercial grade polyol.
    Type: Grant
    Filed: August 24, 1994
    Date of Patent: October 10, 1995
    Inventor: Climent Ho
  • Patent number: 5399784
    Abstract: A high quality bisphenol A with a high purity and an excellent hue is produced from a crystalline adduct of bisphenol A and phenol by washing the adduct with specifically purified phenol, followed by decomposition of the washed adduct to separate bisphenol A. The purification is performed by a method including contacting raw material phenol with a strong-acid ion exchange resin to obtain treated phenol, and distilling the treated phenol.
    Type: Grant
    Filed: September 23, 1993
    Date of Patent: March 21, 1995
    Assignee: Chiyoda Corporation
    Inventors: Sachio Asaoka, Noriyuki Yoneda, Kouji Sakashita, Tetsuo Maejima, Makoto Yasui, Akio Shindo
  • Patent number: 5382711
    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: 5371304
    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: December 6, 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 Kukudome, Ryuichi Inaba, Takashi Imazeki, Karou Shimogawara
  • Patent number: 5344528
    Abstract: Phenol plant waste water containing small amounts of phenol and sodium sulfate is successfully distilled through the addition of recovered sodium sulfate to enhance the volatility of the phenol relative to water; at least a portion of the sodium sulfate is recycled, while a significant portion of the phenol can be returned to the phenol plant for recovery.
    Type: Grant
    Filed: August 4, 1993
    Date of Patent: September 6, 1994
    Assignee: Aristech Chemical Corporation
    Inventors: Thomas H. Bossler, Donald Glassman, Michael C. Grebinoski, Howard H. Morgan, Jr., Jennifer L. Voss
  • Patent number: 5340937
    Abstract: This invention includes an improved process of converting a phenate to a phenol using acid in which a two phase system having an aqueous phase containing phenate and an organic, phenol-containing, phase are present, the improvement comprising adding the acid to enter the aqueous phase while avoiding contact of the acid and phenol phase. Preferably, with sufficient mixing to substantially surround the organic phase with the aqueous phase. The addition is preferably accomplished by mixing the two phases sufficiently to disperse a small organic (phenol) phase in a (bulk) aqueous phase. Such a process conveniently comprises the steps of: (a) mixing a system containing an organic phenol-containing phase and an aqueous phase sufficiently to substantially surround regions of organic phase with aqueous phase; and (b) adding acid to the aqueous phase; and, optionally, (c) maintaining sufficient mixing to prevent contact of concentrated acid with the organic or phenol phase.
    Type: Grant
    Filed: January 8, 1993
    Date of Patent: August 23, 1994
    Inventors: Edward A. Fraini, George W. Tepera, Malcolm W. McClure
  • Patent number: 5336814
    Abstract: A method is provided for depolymerizing scrap aromatic polycarbonate to salvage component monomers by initially effecting aromatic polycarbonate depolymerization by basic phenolysis to produce a mixture having dihydric phenol, and diarylcarbonate. Recovery of the dihydric phenol is effected by distillation of a crystalline dihydric phenol/phenol adduct. Diarylcarbonate is recovered by distillation of the resulting mother liquor after carboxylic acid treatment.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: August 9, 1994
    Assignee: General Electric Company
    Inventor: Sheldon J. Shafer
  • Patent number: 5336752
    Abstract: A method is provided for producing a phenolic resin represented by the formula (I) ##STR1## wherein R.sup.1 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R.sup.2 is a divalent cyclic hydrocarbon residue having 5 to 18 carbon atoms, p is a number of from 0 to 10 and q is a number of 1 or 2. The method involves reacting a phenol with an unsaturated cyclic hydrocarbon compound having two or more carbon-carbon double bonding in the presence of an acid catalyst; and processing a resulting reaction product by a hydrotalcite compound represented by the formula (II)M.sub.1-x.sup.2+ M.sub.x.sup.3+ (OH).sub.2+x-ny A.sub.y.sup.n-.m(H.sub.2 O)(II)where M.sup.2+ is a divalent, magnesium ion, a divalent zinc ion, a divalent calcium ion, a divalent nickel ion, a divalent cobalt ion, a divalent manganese ion or a divalent copper ion, M.sup.3+ is a trivalent aluminum ion, a trivalent iron ion or a trivalent chromium ion, A.sup.n- is HCO.sub.3.sup.-, CO.sub.3.sup.2- or OH.sup.-, and x, y and m each are 0.
    Type: Grant
    Filed: January 28, 1993
    Date of Patent: August 9, 1994
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Fumiaki Oshimi, Susumu Kubota, Masami Enomoto, Yutaka Otsuki
  • Patent number: 5334774
    Abstract: A process for purifying and recovering phenol present in a mixed solution containing phenol and one or more compounds capable of forming azeotropic mixtures with phenol wherein an additive which is at least one compound belonging to the following groups 1 to 5 is added to the mixed solution and the resulting mixture is distilled:group 1: dialkylene glycols having 2-10 carbon atoms, polyalkylene glycols having 2-10 carbon atoms, and the ethers thereof,group 2: alkanediols having 2-20 carbon atoms,group 3: ethanolamine-type compounds represented by the formula (1) shown below,group 4: lactam compounds represented by the formula (2) shown below,group 5: quinoline, sulfolane, and N,N-dimethylimidazolidinone, ##STR1## wherein R.sub.1 represents an alkyl group having 1-6 carbon atoms, a cycloalkyl group having 1-6 carbon atoms, a monohydroxyalkyl group having 1-6 carbon atoms or a hydrogen atom, m represents an integer of 1-4, and X represents a hydroxyl group, an amino group or a hydrogen atom provided that R.sub.
    Type: Grant
    Filed: May 24, 1993
    Date of Patent: August 2, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kayoko Kogure, Kazuo Kimura, Michihiro Kawasaki, Masaaki Toma, Eiji Imamura
  • Patent number: 5264085
    Abstract: A method of continuously distilling off the components of a mixture containing phenols, water and methanol using a single distillation column, wherein methanol is recovered from the top of the column, water containing phenols is dragged as a side stream from a recovery section of the column, and phenols are recovered as a bottom product. The method permits efficient separation by the single distillation column of the three components with high purity and low utility energy.
    Type: Grant
    Filed: August 20, 1992
    Date of Patent: November 23, 1993
    Assignee: Mitsubishi Petrochemical Company, Ltd.
    Inventors: Masashi Inaba, Yoshikazu Higaki, Kimikatsu Jinno, Mitsugi Kataoka, Norio Sato, Masayuki Honda
  • Patent number: 5254750
    Abstract: A process is described for the removal of guaiacol and substituted guaiacols from naturally occurring cresylic acid feed by heating the feed with a strong base, particularly sodium hydroxide, to produce a purified cresylic acid product essentially free of guaiacol and other methoxy aromatic compounds without significant loss of cresylic acid product.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: October 19, 1993
    Assignee: Merichem Company
    Inventor: John A. Waters
  • Patent number: 5243093
    Abstract: A method comprising purifying impure bisphenol-A by fractional melt crystallization in a falling film dynamic crystallizer.
    Type: Grant
    Filed: April 8, 1991
    Date of Patent: September 7, 1993
    Assignee: General Electric Company
    Inventors: Gaylord M. Kissinger, Nicholas P. Wynn
  • Patent number: 5202505
    Abstract: Crude hydroxyphenylalkane, e.g., 1,1,1-tris(4'-hydroxyphenyl)ethane, is purified, to reduce color and prevent caustic solution turbidity, (a) by contacting the hydroxyphenylalkane in alcoholic solution with an alkali metal dithionite, preferably in the presence of an alkalinity agent such as an alkali metal borohydride, more preferably by introducing the dithionite into the alcoholic solution as an alkaline aqueous solution, (b) precipitating the hydroxyphenylalkane from the alcoholic solution, and optionally (c) rinsing the hydroxyphenylalkane with an alkaline aqueous solution of the dithionite.
    Type: Grant
    Filed: March 24, 1992
    Date of Patent: April 13, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Mark A. Murphy, Mike R. Czarny
  • 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: 5177269
    Abstract: A process is described for the removal of guaiacol from naturally occurring cresylic acid feed by heating the feed with a strong acid, particularly hydrochloric acid or sulfuric acid, to produce a purified cresylic acid product essentially free of guaiacol and other methoxy aromatic compounds without significant loss of cresylic acid product.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: January 5, 1993
    Assignee: Merichem Company
    Inventors: John A. Waters, James A. Brient
  • Patent number: 5175376
    Abstract: The object of the invention is a new method for the purification of 2,6-diisopropyl phenol (propofol). The invention is characterized in that the raw product obtained from the alkylation of propene with phenol is crystallized at a temperature where propofol crystallizes but the isomers and other phenol derivatives formed in the reaction are still in liquid form, i.e. at a temperature of -25.degree. to +18.degree. C. especially at -20.degree. to -10.degree. C., without a solvent or using a suitable solvent, such as hexane or petrol ether.
    Type: Grant
    Filed: April 30, 1992
    Date of Patent: December 29, 1992
    Assignee: Leiras Oy
    Inventors: Kauko Nieminen, Peter Essen
  • Patent number: 5171895
    Abstract: Purification of cresylic acid by guaiacol removal from lignite-based feed as well as other naturally occurring sources of cresylic acid is accomplished by catalytic demethylation in the presence of an alumina catalyst. In the process of this invention, de-pitched, dephenolated creyslic acid is vaporized and passed over a high surface area, alumina catalyst at temperature ranges of between 350.degree. C. to 400.degree. C. and at vapor flow rates measured as liquid hourly space velocity (LHSV), of about 1 hr..sup.-1 to demethylate the guaiacol.
    Type: Grant
    Filed: March 23, 1992
    Date of Patent: December 15, 1992
    Assignee: Merichem Company
    Inventor: James A. Brient
  • Patent number: 5146010
    Abstract: A process for removing guaiacols from naturally-occurring cresylic acid mixtures by pyrolysis is described.
    Type: Grant
    Filed: August 9, 1991
    Date of Patent: September 8, 1992
    Assignee: Merichem Company
    Inventors: James A. Brient, Marvin H. Strunk, Jr.
  • Patent number: 5131984
    Abstract: The process for rectification of phenol prepared from crude phenol being the product of decomposition of cumene hydroperoxide and having previously been distilled to remove large portions of acetone, cumene and alpha methylstyrene which includes:feeding the column overhead vapors to a condenser, thereby condensing a major portion of the overhead vapors;withdrawing a small portion of the overhead vapors from the condenser while still in a vapor state, the small portion being relatively enriched in lights and laden with light acids;returning the condensate from the condenser to the phenol distillation column as reflux; andwithdrawing product phenol from at least one-theoretical stage below the top of the phenol distillation column, the product phenol having improved clarity when dispersed in water, clarity being at least 93 percent light transmission as measured by an electrophotometer in a water light test.
    Type: Grant
    Filed: September 23, 1991
    Date of Patent: July 21, 1992
    Assignee: Allied-Signal Inc.
    Inventors: Chong H. Chan, William B. Fisher, Joseph D. Shrom
  • Patent number: 5124490
    Abstract: Acid contaminants leached from acidic ion-exchange resins and carried in process streams with phenol are separated from the phenol by passing the process stream in contact with an anionic exchange resin, whereby the acid contaminants react with and bond to the anionic exchange resin.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: June 23, 1992
    Assignee: General Electric Company
    Inventor: Michael J. Cipullo
  • Patent number: 5087771
    Abstract: A process for producing food-grade tertiary-butyl hydroquinone from impure montertiary butyl hydroquinone is provided. Impure monotertiary butyl hydroquinone crystals are agitated at an elevated temperature while in contact with a non-polar solvent under conditions to extract the majority of the impurities followed by separating purified monotertiary butyl hydroquinone crystals from the solvent at a temperature above the crystallization point of the impurities.
    Type: Grant
    Filed: December 5, 1990
    Date of Patent: February 11, 1992
    Assignee: Eastman Kodak Company
    Inventor: James R. Hilderbrand
  • Patent number: 5064507
    Abstract: High purity phenol is obtained from cleavage of cumene hydroperoxide by treating the crude phenol product stream in a first treatment zone with an amine, a coarse distillation to obtain an overhead stream comprising phenol, alpha-methyl styrene, cumene, and impurities, and steam distillation of the overhead stream in combination with addition of an amine to the steam distillation column for a second amine treatment step.
    Type: Grant
    Filed: September 27, 1990
    Date of Patent: November 12, 1991
    Assignee: Allied-Signal Inc.
    Inventors: Michael S. O'Donnell, Lamberto Crescentini
  • Patent number: 4992599
    Abstract: Crude phenol and also individual phenol fractions from tars or the hydrogenation of coal are purified from contaminating organic bases and sulfur compounds by treating the phenols with phthalic acid anhydride and optionally a quinone and distillation.
    Type: Grant
    Filed: December 13, 1989
    Date of Patent: February 12, 1991
    Assignee: Rutgerswerke AG
    Inventors: Jorg Talbiersky, Bernhard Wefringhaus, Konrad Stolzenberg, Wolfgang Bergins
  • Patent number: 4987273
    Abstract: The invention relates to a process for the separation of a phenol from a mixture obtained by the carboxylation of the phenol and containing phenol, phenolate and the carboxylation products thereof, which process comprises separation carried out by selectively absorbing the phenol into the wall of a membrane, solubilizing the phenol in the membrane matrix, diffusing the phenol through the membrane and desorbing the phenol from the other wall.
    Type: Grant
    Filed: November 21, 1989
    Date of Patent: January 22, 1991
    Assignee: Shell Oil Company
    Inventors: Johan G. A. Bitter, Johannes L. W. C. den Boestert, Wilhelmus J. M. Weeres
  • Patent number: 4973766
    Abstract: A process for recovering phenol from a rectification purge containing various organic foreign matters, which includes the steps of subjecting the purge to an extraction operation, using, as an extracting solvent, an aqueous solution of an alkali metal phenate.
    Type: Grant
    Filed: October 23, 1989
    Date of Patent: November 27, 1990
    Assignee: Montedipe S.r.l.
    Inventors: Renzo Penzo, Paolo Reggiani, Claudio Spaggiari
  • Patent number: 4950805
    Abstract: A process for washing and obtaining solids of a slurry comprises feeding a slurry containing the adduct of bisphenol A with phenol crystallized from a phenol solution of bisphenol A to a first solid-liquid separator to separate solids from the slurry, transferring the solids separated by the first solid-liquid separator to an agitation tank in which the solids are reslurried, feeding the slurry obtained in the agitation tank to a second solid-liquid separator, said second solid-liquid separator being intended to obtain the solids from the slurry discharged from the agitation tank, and permitting the admission of a washing solvent to wash the solids, and permitting the filtrate and washings to be recovered independently, feeding the washing solvent to the second solid-liquid separator, feeding all of the washings from the second solid-liquid separator to the agitation tank, feeding a part of the filtrate from the second solid-liquid separator to the agitation tank, and discharging the remainder of the filtrate
    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: 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: 4929770
    Abstract: Aluminum phenoxide catalyst is removed from a phenolic alkylation mixture by adding 15-30 moles of water per mole of aluminum phenoxide to the alkylation mixture and holding at about 30.degree.-100.degree. C. for 10-60 minutes to form solids and heating the wet mixture to 120.degree.-160.degree. C. and holding at that temperature until filterable particulates form. The particulates can be readily filtered to obtain a substantially aluminum-free filtrate.
    Type: Grant
    Filed: March 8, 1989
    Date of Patent: May 29, 1990
    Assignee: Ethyl Corporation
    Inventors: Charles W. Matthews, Eric S. Batman, Jeffrey F. King
  • Patent number: 4927978
    Abstract: A process for the preparation of crystals of an adduct of a bisphenol with a phenol which comprises:(a) adding an inert volatile liquid hydrocarbon diluent and 0-1.5% weight water to a crude mixture of the bisphenol and the phenol at a temperature above the boiling temperature of the added volatile liquid diluent; and(b) allowing the volatile liquid diluent to boil in the process, thereby cooling the resulting mixture of bisphenol and phenol to a temperature at which adduct crystals form.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: May 22, 1990
    Assignee: Shell Oil Company
    Inventors: James L. Buechele, Edward L. Nielsen, Walter Dong, Paul V. Shaw
  • Patent number: 4927973
    Abstract: A process for the continuous purification of crude bisphenol which comprises (1) forming a single liquid phase comprising a hot mixture of crude bisphenol and water in a ratio substantially of from about 75% to about 85% weight of crude bisphenol to about 15% to about 25% weight water; (2) continuously feeding this mixture together with a stream of warm water to a first crystallization zone at a temperature sufficient to maintain a bisphenol-rich liquid phase, a water-rich phase and a crystalline phase comprising about 70% to about 95% of the total bisphenol in the mixture; (3) passing the three-phase mixture of bisphenol and water to a second crystallization zone operated at about 85.degree. C. to about 97.degree. C. until about 90% to about 99% of the total bisphenol is crystallized; and (4) recovering the purified bisphenol crystals.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: May 22, 1990
    Assignee: Shell Oil Company
    Inventors: Walter Dong, Paul V. Shaw, James L. Buechele
  • Patent number: 4857151
    Abstract: Crude phenol containing methyl benzofuran and other impurities is distilled in the presence of water to recover a phenol bottoms having a reduced quantity of impurities. The water-phenol overhead is cooled to separate a water phase essentially free of methyl benzofuran, which is recycled to the distillation. The organic phase may then be further distilled, in the presence of water, as previously described, to eventually recover a reduced quantity of phenol in which impurities are concentrated.
    Type: Grant
    Filed: June 28, 1982
    Date of Patent: August 15, 1989
    Assignee: The Lummus Company
    Inventors: George D. Suciu, Ali M. Khonsari, Jamin Chen
  • Patent number: 4855053
    Abstract: Process for extracting organic compounds which are present in water in the form of solutions or suspensions by a liquid carboxylic acid which is immiscible with water. Branched or unbranched linear acids such as n-heptanoic, n-octanoic, or 2-ethylhexanoic acids make it possible to quantitatively extract compounds such as phenols, amines or amino acids from such aqueous solutions, thereby rendering the process useful for the purification of industrial wastewaters.
    Type: Grant
    Filed: December 18, 1986
    Date of Patent: August 8, 1989
    Assignee: Atochem
    Inventors: Charles Benedetti, Claude Gluntz, Robert Pascal, Michel Stefanini
  • 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: 4827050
    Abstract: Coal tar oil is separated quantitatively into neutral oil, phenols and bases by a two stage extraction with overcritical gases. Carbon dioxide is employed as an overcritical extraction agent, and propane or butane are preferably added as entrainers. The neutral oil is obtained in the first stage. Tar bases can be employed as an additional entrainer for improving the selectivity. The bases are extracted in the second stage. The method is associated with the advantage that it saves energy and that no byproducts are generated.
    Type: Grant
    Filed: March 13, 1987
    Date of Patent: May 2, 1989
    Assignee: Rutgerwerke Aktiengesellschaft
    Inventors: Siegfried Peter, Marc Seekamp, Herbert Beneke, Jurgen Stadelhofer
  • Patent number: 4806210
    Abstract: A process for the recovery of alcohols and hydrogen sulfide from a thiophosphate containing mixture is disclosed.
    Type: Grant
    Filed: September 11, 1987
    Date of Patent: February 21, 1989
    Assignee: The Lubrizol Corporation
    Inventor: Frank M. Van Lier
  • Patent number: 4795829
    Abstract: A process for separating higher molecular weight constituents from phenol polymers, wherein the phenol polymer is dissolved in an organic solvent medium, the solution obtained is mixed at room temperature with ammonia or an amine such that there is a stoichiometric deficiency of ammonia or amine, the precipitate is separate, dried, if appropriate, and treated with aqueous acid, and the resulting sediment is filtered off, washed and dried as described. The starting phenol polymer preferably is a condensation product of optionally substituted phenol and formaldehyde. The process yields fractions possessing an increased osmometric molecular weight, a narrower molecular weight distribution range and an increased glass transition temperature.
    Type: Grant
    Filed: March 16, 1987
    Date of Patent: January 3, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Arnold Schneller, Gabriele Lambert
  • Patent number: 4769499
    Abstract: A substituted benzene isomer mixture containing a meta-substituted benzene or 1,3,5-substituted benzene is contacted with an adsorbent of a faujasite type zeolite containing a Ag cation and/or a Cu cation, whereby the meta-substituted benzene or 1,3,5-substituted benzene is separated and recovered as a raffinate component.
    Type: Grant
    Filed: May 12, 1987
    Date of Patent: September 6, 1988
    Assignee: Toray Industries, Inc.
    Inventors: Kishio Miwa, Yukiko Nagaoka, Takehise Inoue
  • 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: 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: 4720596
    Abstract: A process for removing phenol from water which comprises contacting a phenol bearing water stream with a bisphenol-A melt thereby separating phenol from the water.
    Type: Grant
    Filed: December 9, 1986
    Date of Patent: January 19, 1988
    Assignee: General Electric Company
    Inventors: Gaylord M. Kissinger, Isabel M. Gomes de Matos
  • Patent number: 4695410
    Abstract: The disclosed process is employed to recover phenol from aqueous solutions produced by distillation of the product of a process for producing a phenyl ester by the reaction of a carboxylic acid and phenol. Purified phenyl ester is employed to extract phenol from the aqueous solution. The extract is combined with raw product for recovery of the phenol and phenyl ester. In a preferred embodiment the process for producing the phenyl ester is continuous and the extract containing phenol and phenyl ester are fed to the dewatered ester stream for product recovery.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: September 22, 1987
    Assignee: Monsanto Company
    Inventors: Gary J. Lynch, Chen-Hsyong Yang
  • Patent number: 4686010
    Abstract: The production of solutions of hydrogen peroxide in phenol or its derivatives, e.g. hydrocarbyl substituted phenols, halo substituted phenols or phenol ethers, is carried out in a single step. Practically no loss of hydrogen peroxide occurs since a total distillation of hydrogen peroxide together with phenol or phenol derivative is avoided. Simultaneously the solutions obtained are practically free from water. The mixture of phenol or phenol derivative and aqueous hydrogen peroxide is treated with a material that boils below the boiling point of hydrogen peroxide, phenol or phenol derivative or forms an azeotrope with water that boils below the boiling point of hydrogen peroxide, phenol or phenol derivative and the water removed as an azeotrope. The solution of hydrogen peroxide in phenol or phenol derivative which remains behind is suitable for carrying out oxidation reactions and above all, also for hydroxylation reactions.
    Type: Grant
    Filed: September 7, 1984
    Date of Patent: August 11, 1987
    Assignee: Degussa Aktiengesellschaft
    Inventors: Karlheinz Drauz, Axel Kleemann
  • Patent number: 4634796
    Abstract: Phenol feed to a steam distilling column, containing alpha-methylstyrene and mesityl oxide, is treated with a base, without acidification, and the heavy phenol product is acidified and distilled in a high purity column to recover high purity phenol as a sidestream and lighter components as overhead. Acidification after steam distilling, rather than prior to steam distilling, increases phenol recovery by reducing the overhead pasteurizing cut from the high purity column.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: January 6, 1987
    Assignee: Lummus Crest, Inc.
    Inventors: George D. Suciu, Ali M. Khonsari
  • Patent number: 4626605
    Abstract: The invention relates to a process for extracting phenols from aqueous solutions. The extractant used is a salt of an aliphatic amine, having a total carbon number of at least 10, and a strong acid.
    Type: Grant
    Filed: October 2, 1985
    Date of Patent: December 2, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Bernhard Wojtech, Manfred Mayer, Karl-Erich Ott