Preparation By Hydrolysis Of Amide, Anhydride, Or Ester Patents (Class 562/483)
  • Patent number: 9150485
    Abstract: Processes have been developed for oxidizing alkyl aromatic compounds, and which reduce the amount of 4-CBA in the solid oxidation products. The process can reduce the makeup amount of ionic liquid, carboxylic acid, catalyst, bromine source, and ammonia source.
    Type: Grant
    Filed: October 8, 2013
    Date of Patent: October 6, 2015
    Assignee: UOP LLC
    Inventors: Avram M. Buchbinder, Raymond Shih, Alakananda Bhattacharyya, Evan B. Jorgenson, Tatsamai Jarusiripipat, Nina Kuznetsova
  • Publication number: 20110257361
    Abstract: Disclosed is a 5-alkyl-1,2,3,4-benzene tetracarboxylic-1:2,3:4-dianhydride which is represented by the general formula (1) and has excellent solubility with respect to various organic solvents. Depending on the diamine that is used, a polyimide with excellent heat resistance or a polyimide with good workability at a low melting point can be provided, and in addition, a polyimide that exhibits excellent characteristics for electronic materials or the like can be provided. (In the formula, R1 represents an alkyl group with carbon number 1-10.
    Type: Application
    Filed: December 17, 2009
    Publication date: October 20, 2011
    Inventors: Hideo Suzuki, Takayuki Tamura, Takahiro Noda
  • Publication number: 20110172461
    Abstract: Methods of recycling a post-consumer polymer material comprise depolymerizing the polymer material by heating the polymer material in the presence of a hydrogen donor material and a strong base compound, and optionally a catalyst, to effect catalytic transfer hydrogenation and base cleavage and produce intermediate and/or monomer products of molecular weights lower than that of the polymeric material. In a specific embodiment, the methods comprise recycling post-consumer polyethylene terephthalate. The methods comprise depolymerizing the polyethylene terephthalate by heating in the presence of a hydrogen donor material and a strong base compound, and optionally a catalyst, to effect catalytic transfer hydrogenation and base cleavage and produce terephthalic and/or naphthalic acid, or a salt thereof, and ethylene glycol.
    Type: Application
    Filed: September 8, 2008
    Publication date: July 14, 2011
    Inventor: Charles J. Rogers
  • Patent number: 7893152
    Abstract: Methods of making a modified pigment by reacting a first chemical group and a second chemical group to form a pigment having attached a third chemical group. The first chemical group includes at least one nucleophile and the second chemical group includes at least one electrophile, or vice versa. Resulting modified pigments, and ink compositions containing such pigments, are also described.
    Type: Grant
    Filed: February 27, 2004
    Date of Patent: February 22, 2011
    Assignee: Cabot Corporation
    Inventors: Paul S. Palumbo, Curtis E. Adams
  • Patent number: 7799837
    Abstract: There are provided a bottle which has a laminate structure including a glycolic acid polymer layer showing good gas-barrier property in addition to a principal resin layer and is yet provided with excellent recyclability, and also an efficient method of recycling the bottle. More specifically, a bottle having a laminate structure including at least one layer of glycolic acid polymer in addition to a principal resin layer, is obtained. After breaking the bottle, the broken pieces are washed with alkaline water, water or acidic water to remove the glycolic acid polymer layer, thereby recovering the principal resin.
    Type: Grant
    Filed: September 16, 2008
    Date of Patent: September 21, 2010
    Assignee: Kureha Corporation
    Inventors: Kazuyuki Yamane, Ryo Kato, Hiroyuki Sato
  • Patent number: 7585930
    Abstract: A method of decomposing a polycarbonate with water in a supercritical or subcritical state. A high-purity dihydroxy compound which is a constituent component of the polycarbonate can be recovered at a high yield by this decomposition method. This decomposition method is environment-friendly because it does not use an organic solvent, easy to be carried out, has a high decomposition rate and rarely causes a side reaction.
    Type: Grant
    Filed: February 8, 2005
    Date of Patent: September 8, 2009
    Assignee: Teijin Limited
    Inventors: Mai Kitahara, Masumi Hirata, Tetsuo Ban, Toru Sawaki
  • Publication number: 20090171113
    Abstract: A process for ethanolysis of PET is disclosed wherein a feed comprising PET is reacted with ethanol and recovering ethylene glycol and an aromatic diethyl ester such as diethyl isophthalate and/or diethyl terephthalate. PET, or a terpolymer comprising terephthalate monomer and ethylene glycol monomers, is reacted with ethanol and ethanol, diethyl terephthalate, ethylene glycol and optionally diethyl isophthalate are recovered. Recovered diethyl components can be subjected to liquid-phase oxidation to produce aromatic carboxylic acid. Acetic acid may also produced via liquid-phase oxidation of recovered diethyl components. The aromatic carboxylic acid can be used to form polymer.
    Type: Application
    Filed: December 30, 2006
    Publication date: July 2, 2009
    Applicant: BP Corporation North America Inc.
    Inventors: Ronald L. Anderson, David L. Sikkenga
  • Publication number: 20090099388
    Abstract: The present invention relates to a process of recovering aromatic dicarboxylic acids with low metal contaminants from manufactured articles, such as beverage bottles, fibers and films, comprising aromatic polyesters, whether or not those articles are contaminated with PVC or chlorinated compounds, or from waste from processing of these polyesters. In particular, the invention relates to the recovery of terephthalic acid, isophthalic acid and 2,6-naphthalene dicarboxylic acid from bottles for recycling which are made of PET, PEN or aromatic polyester copolymers.
    Type: Application
    Filed: April 3, 2006
    Publication date: April 16, 2009
    Inventors: Hussain Al Ghatta, Milan Hronec
  • Patent number: 7173150
    Abstract: This invention provides a process a process for recovering terephthalic acid from pulverized products of spent polyethylene terephthalate.
    Type: Grant
    Filed: April 24, 2003
    Date of Patent: February 6, 2007
    Assignee: Tsukishima Kikai Co., Ltd.
    Inventors: Jinichi Yazaki, Kozaburo Sakano, Nobuyuki Funakoshi, Kazuho Tanaka
  • Patent number: 7041199
    Abstract: A process and a device for the catalytic hydrolysis of a carboxylate, e.g., methyl acetate, ethyl acetate, i- or n-propyl acetate, i- or n-butyl acetate, allyl acetate and methyl formate, into the corresponding carboxylic acid and alcohol, by a combination of a pre-reactor and a reactive distillation column are disclosed. By the combination of a pre-reactor and a reactor distillation column, the conversion ratio can be substantially improved. The device can compensate for fluctuations in the supply quantity or in the composition of the feed flow. The product composition can also be controlled in a wide range.
    Type: Grant
    Filed: October 11, 2000
    Date of Patent: May 9, 2006
    Assignees: Sulzer Chemtech AG, Wacker Chemie GmbH
    Inventors: Peter Moritz, Franz Ramgraber, Claudia von Scala, Harald Michl
  • Patent number: 6720448
    Abstract: The present invention relates to a method of recovering a solution comprising the chemical species obtained by depolymerization of PET from a material containing poly(ethylene terephthalate) in the form of bottles, by making said material react, in the absence of water, with a reagent consisting of one or more metal salts of a weaker acid than the terephthalic acid and of ethylene glycol, until a water-soluble intermediate product is obtained, and subsequently carrying out dissolution in water, stirring and filtering.
    Type: Grant
    Filed: October 2, 2001
    Date of Patent: April 13, 2004
    Inventor: Massimo Broccatelli
  • Patent number: 6670503
    Abstract: The present invention relates to a method of recovering terephthalic acid from a material containing poly(ethylene terephthalate) (P.E.T.) in the form of bottles, by making said material react, in the absence of water, with a reagent consisting of one or more metal salts of a weaker acid than the terephthalic acid, until a water-soluble compound is obtained, and subsequently carrying out dissolution in water and acidification.
    Type: Grant
    Filed: February 21, 2001
    Date of Patent: December 30, 2003
    Inventor: Massimo Broccatelli
  • Publication number: 20030225299
    Abstract: This invention provides a process a process for recovering terephthalic acid from pulverized products of spent polyethylene terephthalate.
    Type: Application
    Filed: April 24, 2003
    Publication date: December 4, 2003
    Applicant: Tsukishima Kikai Co., Ltd.
    Inventors: Jinichi Yazaki, Kozaburo Sakano, Nobuyuki Funakoshi, Kazuho Tanaka
  • Patent number: 6657077
    Abstract: The invention concerns a method for producing terephthalate of alkaline metal and alkylene glycol from recuperated alkylene polyterephthalate. It comprises saponification of said alkylene terephthalates with an aqueous sodium solution, adding a sufficient volume of water to ensure solubilization of the entire alkaline metal terephthalate produced in the reaction medium liquid phase and crystallisation of the sodium terephthalate by concentration of said liquid phase. The resulting sodium terephthalate can be directly used for producing pure terephthalic acid usable for the renewed production of alkylene polyterephthalates to be used in the food industry.
    Type: Grant
    Filed: November 16, 2000
    Date of Patent: December 2, 2003
    Assignee: Tredi
    Inventors: Jacques Thauront, Laurent Bonnamich, Guy Fraysse
  • Patent number: 6649792
    Abstract: The proposed method of chemical recycling of polyethylene terephthalate waste to terephthalic acid and ethandiol is based on a continuous series of gradual steps, namely (a) separation of the polyethylene terephthalate component of the input material by its conversion to brittle form through crystallization, grinding and subsequent sifting, followed by (b) continuous two-stage hydrolysis of the polyethylene terephthalate, carried out in the first stage by feeding steam to the polymer melt, and in the second stage, by the reaction of the products of the first stage of hydrolysis with ammonium hydroxide, followed by (c) condensation of terephthalic acid from an aqueous solution of the second-stage hydrolysis products by inorganic acid, and its separation by means of filtration, and finally (d) rectification separation of ethandiol from a solution of the products of the second stage of hydrolysis, after the separation of terephthalic acid.
    Type: Grant
    Filed: September 13, 2002
    Date of Patent: November 18, 2003
    Inventors: Milan {haeck over (S)}irek, Jaroslav Jirou{haeck over (s)}ek
  • Patent number: 6580005
    Abstract: This invention provides a process a process for recovering terephthalic acid from pulverized products of spent polyethylene terephthalate.
    Type: Grant
    Filed: November 22, 2000
    Date of Patent: June 17, 2003
    Assignee: Tsukishima Kikai Co., Ltd.
    Inventors: Jinichi Yazaki, Kozaburo Sakano, Nobuyuki Funakoshi, Kazuho Tanaka
  • Patent number: 6562877
    Abstract: A method for the recovery of dicarboxylic aromatic acids, in particular terephthalic acid, from manufactured aromatic polyester-resin articles for recycling, wherein the article, fragmented into chip form, is reacted in solution in a carboxylic acid with 2-6 carbon atoms and with a pKa from 4 to 6, preferably glacial acetic acid, in the presence of catalytic quantities of a strong acid with a pKa of less than 1, preferably aqueous hydrochloric acid or sulfuric acid, operating at temperatures from 160° to 250° C.
    Type: Grant
    Filed: December 11, 2001
    Date of Patent: May 13, 2003
    Assignee: Sinco Ricerche S.p.A.
    Inventor: Hussain Al Ghatta
  • Patent number: 6521783
    Abstract: This invention relates in part to a processes for the conversion of a feedstock stream comprising carbon monoxide and hydrogen to a product stream comprising at least one of an ester, acid, acid anhydride and mixtures thereof. This invention also relates in part to processes for converting an alcohol and/or ether feedstock to oxygenated products, e.g., esters, acids, acid anhydrides and mixtures thereof. The processes and catalysts are especially suitable for the production of acetic acid and methyl acetate from a synthesis gas feedstock or from an alcohol and/or ether feedstock.
    Type: Grant
    Filed: July 10, 2000
    Date of Patent: February 18, 2003
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Richard William Wegman, David McNeill Somerville, Barry Brent Fish, Raymond Edwin Rooks, Chinsoo Stephen Lee, Paul Frank Bryan, William J. Bartley, David Michael Anthony Minahan, Fungau Ho
  • Publication number: 20030032840
    Abstract: The proposed method of chemical recycling of polyethylene terephthalate waste to terephthalic acid and ethandiol is based on a continuous series of gradual steps, namely (a) separation of the polyethylene terephthalate component of the input material by its conversion to brittle form through crystallization, grinding and subsequent sifting, followed by (b) continuous two-stage hydrolysis of the polyethylene terephthalate, carried out in the first stage by feeding steam to the polymer melt, and in the second stage, by the reaction of the products of the first stage of hydrolysis with ammonium hydroxide, followed by (c) condensation of terephthalic acid from an aqueous solution of the second-stage hydrolysis products by inorganic acid, and its separation by means of filtration, and finally (d) rectification separation of ethandiol from a solution of the products of the second stage of hydrolysis, after the separation of terephthalic acid.
    Type: Application
    Filed: September 13, 2002
    Publication date: February 13, 2003
    Inventors: Milan Sirek, Jaroslav Jirousek
  • Patent number: 6472557
    Abstract: A process for producing high quality TPA suitable for PET feedstock material from recycled polyester. The process includes the steps of depolymerizing the polyester to form DMT; separating the DMT from secondary materials; and hydrolyzing the DMT to form TPA. In a preferred embodiment of the invention the recycled polyester is contacted with a component monomer or oligomer thereof to liquefy the polyester prior to depolymerizing the polyester.
    Type: Grant
    Filed: November 12, 1999
    Date of Patent: October 29, 2002
    Assignee: Eastman Chemical Company
    Inventors: Thomas Michael Pell, Jr., Michael Paul Ekart, David Dunlap Cornell, Damon Brian Shackelford, Donald Lee Carver
  • Patent number: 6461700
    Abstract: Processes for producing aromatic monomers useful for forming polyesters are disclosed. Cost effective steps employed in the processes permit small amounts of process-related materials typically removed from monomer to remain in an aromatic monomer product. In many cases, the presence of the process-related materials left in the monomer product by the cost effective process steps can enhance the performance of the monomer in certain applications.
    Type: Grant
    Filed: August 23, 2001
    Date of Patent: October 8, 2002
    Assignee: BP Corporation North America Inc.
    Inventors: Edward E. Paschke, Bruce I. Rosen, David A. Peterson, David E. James, Melvin L. Luetkens, Jr., Charles W Bauer, Gary T. Brooks
  • Patent number: 6462230
    Abstract: A method of decomposing wastes containing target compounds having one or more of hydrolyzable bonds of ether bond, ester bond, amide bond and isocyanate bond wherein the method comprises continuously supplying the wastes in a molten state or liquid state to a reactor, continuously supplying super-critical water or high pressure/high temperature water to the reactor, bringing the water into contact with the wastes, thereby decomposing the target compounds and then recovering them as raw material compounds or derivatives thereof for the target compounds. Target compounds contained in wastes in chemical plants which could not be utilized but merely incinerated or discarded so far are continuously decomposed into raw material compounds or derivatives thereof for the aimed compound and can be reutilized effectively.
    Type: Grant
    Filed: August 4, 2000
    Date of Patent: October 8, 2002
    Assignees: Kabushiki Kaisha Kobe Seiko Sho, Takeda Chemical Industries, Ltd.
    Inventors: Yoshiyuki Nagase, Ryuichi Fukuzato
  • Patent number: 6452046
    Abstract: A process for producing 2,3,5,6-tetrachloro-1, 4-benzenedicarboxylic acid, comprising heating 2,3,5,6-tetrachloro-1,4-benzenedicarboxamide together with sulfuric acid exhibiting an acidity function (—Ho) of 10.27 to 14.44 in the presence of water contained in an amount smaller than a stoichiometric value of hydrolysis at 110 to 190° C. This process efficiently produces 2,3,5,6-tetrachloro-1,4-benzenedicarboxylic acid which is a precursor of dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate useful as a herbicide.
    Type: Grant
    Filed: February 22, 2001
    Date of Patent: September 17, 2002
    Assignee: SDS Biotech K.K.
    Inventors: Utaro Matsushita, Kimitoshi Sano, Kenichi Komatsubara, Teruhiko Ishii
  • Publication number: 20020077500
    Abstract: A method for the recovery of dicarboxylic aromatic acids, in particular terephthalic acid, from manufactured aromatic polyester-resin articles for recycling, wherein the article, fragmented into chip form, is reacted in solution in a carboxylic acid with 2-6 carbon atoms and with a pKa from 4 to 6, preferably glacial acetic acid, in the presence of catalytic quantities of a strong acid with a pKa of less than 1, preferably aqueous hydrochloric acid or sulphuric acid, operating at temperatures from 160° to 250° C.
    Type: Application
    Filed: December 11, 2001
    Publication date: June 20, 2002
    Applicant: Sinco Ricerche S.p.A.
    Inventor: Hussain Al Ghatta
  • Publication number: 20020065430
    Abstract: The present invention relates to a method of recovering a solution comprising the chemical species obtained by depolymerization of PET from a material containing poly(ethylene terephthalate) in the form of bottles, by making said material react, in the absence of water, with a reagent consisting of one or more metal salts of a weaker acid than the terephthalic acid and of ethylene glycol, until a water-soluble intermediate product is obtained, and subsequently carrying out dissolution in water, stirring and filtering.
    Type: Application
    Filed: October 2, 2001
    Publication date: May 30, 2002
    Inventor: Massimo Broccatelli
  • Publication number: 20010025121
    Abstract: A process for producing 2,3,5,6-tetrachloro-1,4-benzenedicarboxylic acid, comprising heating 2,3,5,6-tetrachloro-1,4-benzenedicarboxamide together with sulfuric acid exhibiting an acidity function (—Ho) of 10.27 to 14.44 in the presence of water contained in an amount smaller than a stoichiometric value of hydrolysis at 110 to 190° C. This process efficiently produces 2,3,5,6-tetrachloro-1,4-benzenedicarboxylic acid which is a precursor of dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate useful as a herbicide.
    Type: Application
    Filed: February 22, 2001
    Publication date: September 27, 2001
    Applicant: SDS Biotech K.K.
    Inventors: Utaro Matsushita, Kimitoshi Sano, Kenichi Komatsubara, Teruhiko Ishii
  • Patent number: 6284920
    Abstract: Processes for producing aromatic monomers useful for forming polyesters are disclosed. Cost effective steps employed in the processes permit small amounts of process-related materials typically removed from monomer to remain in an aromatic monomer product. In many cases, the presence of the process-related materials left in the monomer product by the cost effective process steps can enhance the performance of the monomer in certain applications. Aromatic monomer products and polymers produced therefrom having these advantages also are disclosed, as well as products such as pasteurizable bottles made from these polymers.
    Type: Grant
    Filed: October 4, 1999
    Date of Patent: September 4, 2001
    Assignee: BP Corporation North America Inc.
    Inventors: Edward E. Paschke, Bruce I. Rosen, David A. Peterson, David E. James, Melvin L. Luetkens, Jr., Charles W. Bauer, Gary T. Brooks
  • Patent number: 6255529
    Abstract: A method of decomposing wastes containing target compounds having one or more of hydrolyzable bonds of ether bond, ester bond, amide bond and isocyanate bond wherein the method comprises continuously supplying the wastes in a molten state or liquid state to a reactor, continuously supplying super-critical water or high pressure/high temperature water to the reactor, bringing the water into contact with the wastes, thereby decomposing the target compounds and then recovering them as raw material compounds or derivatives thereof for the target compounds. Target compounds contained in wastes in chemical plants which could not be utilized but merely incinerated or discarded so far are continuously decomposed into raw material compounds or derivatives thereof for the aimed compound and can be reutilized effectively.
    Type: Grant
    Filed: January 16, 1997
    Date of Patent: July 3, 2001
    Assignees: Kabushiki Kaisha Kobe Seiko Sho, Takeda Chemical Industries, Ltd.
    Inventors: Yoshiyuki Nagase, Ryuichi Fukuzato
  • Patent number: 6255525
    Abstract: A process for preparing an aromatic carboxylic acid having improved purity comprising contacting at an elevated temperature and pressure a mixture comprising an impure aromatic carboxylic acid and a solvent in the presence of hydrogen gas with a carbon catalyst which is essentially free of a hydrogenation metal component.
    Type: Grant
    Filed: December 1, 1998
    Date of Patent: July 3, 2001
    Assignee: BP Amoco Corporation
    Inventors: David Lee Sikkenga, M. Michelle Morie-Bebel, Stephen V. Hoover
  • Patent number: 6248879
    Abstract: A process for preparation of crosslinked cellulosic products containing at least 30 wt. % cellulosic fibers and the polyanhydride crosslinked cellulosic products resulting therefrom wherein a cellulosic material is treated with an aqueous solution of a polycarboxylic acid formed by hydrolysis of a polyanhydride of the structure which comprises the reaction product of trimellitic anhydride and a diol in the mole ratio of from about 2.0:0.9 to about 2.0:1.1, wherein R is selected from the group consisting of alkyl, alkylene and cycloalkylene moieties of up to 12 carbon atoms and ethylene oxide and propylene oxide moieties of molecular weight up to about 6000, wherein said cellulosic material is impregnated with an aqueous solution of said polyanhydride, dried, and heated to a temperature of from about 120° C. to about 200° C.
    Type: Grant
    Filed: August 13, 1999
    Date of Patent: June 19, 2001
    Assignee: BP Amoco Corporation
    Inventors: Ronald L. Anderson, Wendell W. Cattron, Vincent F. Smith, Jr., David J. Fenoglio
  • Patent number: 6239310
    Abstract: A subject of the invention is the method of recovery of terephthalic acid and ethylene glycol from poly/ethylene terephthalate/wastes. According to the invention poly/ethylene terephthalate/ is heated in an aqueous solution at the temperature from 150° C. to 280° C. with a reagent substance, chosen from the group, comprising bicarbonates of ammonia and alkali metals, ammonium carbamate and urea, which substances are used in amounts not less than a stoechiometric amount.
    Type: Grant
    Filed: August 2, 1999
    Date of Patent: May 29, 2001
    Inventor: Heinrich Smuda
  • Patent number: 6103930
    Abstract: This invention concerns a method for recycling polyesters comprising the hydrolysis of polyesters containing repeat units derived from 2,6-naphthalene dicarboxylic acid in the presence of a carboxylic acid which gives pure 2,6-naphthalene dicarboxylic acid suitable for use as a monomer.
    Type: Grant
    Filed: September 18, 1998
    Date of Patent: August 15, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Michael Robert Samuels, Marion Glen Wagonner
  • Patent number: 6075163
    Abstract: This invention relates to a process for manufacturing terephthalic acid and more particularly, to a process for manufacturing terephthalic acid in a high recovery rate with high purity in accordance with the practice of this invention comprising the following procedures: polyethylene terephthalate (hereinafter referred to as "PET") scrap is hydrolyzed with alkaline aqueous solution to give the slurry of terephthalic acid alkali metal/earth metal salt, then the particles of terephthalic acid formed from acid-neutralization are enlarged to recover terephthalic acid with high purity.
    Type: Grant
    Filed: June 29, 1998
    Date of Patent: June 13, 2000
    Assignee: Sunkyong Industries Co., Ltd.
    Inventors: Hang-Duk Roh, Dongmok Bae
  • Patent number: 6031128
    Abstract: This invention relates to a process for manufacturing terephthalic acid and more particularly, to a process of manufacturing and recovering the highly purified terephthalic acid using an alkali weight-reduction waste water discharged from weight-reduction process in a polyester textile dyeing complex, in accordance with the practice of this invention comprising the following procedures: polyethylene terephthalate (hereinafter referred to "PET") waste scrap materials are hydrolyzed to prepare the slurry of disodium terephthalate. Then, said slurry dissolved in water is adsorbed to remove impurities, and followed by acid-neutralization to obtain terephthalic acid of this invention.
    Type: Grant
    Filed: June 29, 1998
    Date of Patent: February 29, 2000
    Assignee: Sunkyong Industries Co., Ltd.
    Inventors: Hang-Duk Roh, Dongmok Bae
  • Patent number: 6013835
    Abstract: A method and apparatus for purifying crude terephthalic acid from a liquid dispersion thereof also containing impurities selected from unreacted starting materials, solvents, products of side reactions and/or other undesired materials is provided. The method comprises the steps of filtering the dispersion to form a crude terephthalic acid filter cake, dissolving the filter cake in a selective crystallization solvent at an elevated temperature to form a solution, crystallizing purified terephthalic acid from the solution in the crystallization solvent by reducing the pressure and temperature of the solution, and separating the crystallized purified terephthalic acid from the solution. According to the invention, the selective crystallization solvent is non-aqueous, non-corrosive and essentially non-reactive with terephthalic acid. Preferably, the selective crystallization solvent is N-methyl pyrrolidone.
    Type: Grant
    Filed: December 6, 1996
    Date of Patent: January 11, 2000
    Assignee: HFM International, Inc.
    Inventors: Fu-Ming Lee, Wiston Lamshing
  • Patent number: 5981739
    Abstract: A process for preparation of crosslinked cellulosic products containing at least 30 wt. % cellulosic fibers and the polyanhydride crosslinked cellulosic products resulting therefrom wherein a cellulosic material is treated with an aqueous solution of a polycarboxylic acid formed by hydrolysis of a polyanhydride of the structure ##STR1## which comprises the reaction product of trimellitic anhydride and a diol in the mole ratio of from about 2.0:0.9 to about 2.0:1.1, wherein R is selected from the group consisting of alkyl, alkylene and cycloalkylene moieties of up to 12 carbon atoms and ethylene oxide and propylene oxide moieties of molecular weight up to about 6000, wherein said cellulosic material is impregnated with an aqueous solution of said polyanhydride, dried, and heated to a temperature of from about 120.degree. C. to about 200.degree. C.
    Type: Grant
    Filed: September 10, 1997
    Date of Patent: November 9, 1999
    Assignee: BP Amoco Corporation
    Inventors: Ronald L. Anderson, Wendell W. Cattron, Vincent F. Smith, Jr., David J. Fenoglio
  • Patent number: 5849949
    Abstract: Alkyl- and arylmalonic acids of the formula I ##STR1## where R.sup.1 =H, C.sub.1 -C.sub.12 -alkyl, phenyl, C.sub.1 -C.sub.4 -alkylphenyl, C.sub.2 -C.sub.4 -dialkylphenyl,R.sup.2 =C.sub.1 -C.sub.12 -alkyl, phenyl, C.sub.1 -C.sub.4 -alkylphenyl, C.sub.2 -C.sub.4 -dialkylphenyl orR.sup.1 +R.sup.2 =--CH.sub.2 --CH.sub.2 --, are prepared by alkaline saponification by hydrolyzing the corresponding C.sub.1 -C.sub.4 -alkyl esters of the malonic acid of formula I, with alkali metal hydroxide dissolved in an aqueous alkali metal salt solution containing salt at 90-100% of saturation, acidifying the hydrolysis product with a mineral acid, removing the precipitated alkali metal salt which forms upon acidification, and extracting the alkyl- and arylmalonic acid formed from the aqueous solution with the aid of an organic solvent.
    Type: Grant
    Filed: April 21, 1998
    Date of Patent: December 15, 1998
    Assignee: Huels Aktiengesellschaft
    Inventor: Klaus-Dieter Steffen
  • Patent number: 5767311
    Abstract: A method and apparatus for purifying crude terephthalic acid from a liquid dispersion thereof also containing impurities selected from unreacted starting materials, solvents, products of side reactions and/or other undesired materials is provided. The method comprises the steps of filtering the dispersion to form a crude terephthalic acid filter cake, dissolving the filter cake in a selective crystallization solvent at an elevated temperature to form a solution, crystallizing purified terephthalic acid from the solution in the crystallization solvent by reducing the temperature of the solution, and separating the crystallized purified terephthalic acid from the solution. According to the invention, the selective crystallization solvent is non-aqueous, non-corrosive and essentially non-reactive with terephthalic acid. Preferably, the selective crystallization solvent is N-methyl pyrrolidone.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: June 16, 1998
    Assignee: Glitsch International, Inc.
    Inventors: Fu-Ming Lee, Wei-Teh Wade Shang
  • Patent number: 5750776
    Abstract: Dicarboxylic acids or esters thereof are recovered from solid phase polyester materials, such as post-consumer products and factory scrap, by initially subjecting the polyester to a glycolysis reaction (in one or more stages) to produce a liquid phase medium containing depolymerisation products. The liquid phase medium is then contacted with aqueous medium or alcohol in one or ore stages to produce the dicarboxylic acid or an ester thereof together with glycol.
    Type: Grant
    Filed: December 18, 1995
    Date of Patent: May 12, 1998
    Assignee: Imperial Chemical Industries PLC
    Inventor: James Lumsden Harvie
  • Patent number: 5731459
    Abstract: The invention relates to a process for removing amino acids and/or aminosulphonic acids from preferably aqueous solutions which contain these as impurities by adsorbing the amino acids on zeolites. Solutions to which the process according to the invention can be applied are produced, for example, from the industrial synthesis of oligopeptides in which the amino acids serving as starting materials are always present in solution, sometimes to a not inconsiderable residual concentration, together with the desired end product.
    Type: Grant
    Filed: August 28, 1996
    Date of Patent: March 24, 1998
    Assignee: Degussa Aktiengesellschaft
    Inventors: Stefan Stockhammer, Wiltrud Schafer-Treffenfeldt, Gunter Knaup, Karlheinz Drauz, Elfriede Sextl
  • Patent number: 5728870
    Abstract: A process for preparing purified 2,6-naphthalenedicarboxylic acid which comprises hydrolyzing a dialkyl-2,6-naphthalenedicarboxylate with water at a reaction temperature of at least about 450.degree. F. under liquid phase condition, the amount of water present being sufficient to solubilize, at the reaction temperature, at least about 10 percent of the 2,6-naphthalenedicarboxylic acid formed; and a process for purifying 2,6-naphthalenedicarboxylic acid comprising combining impure 2,6-naphthalenedicarboxylic acid with a purification solvent, heating the resulting mixture under liquid phase conditions at a temperature of at least about 500.degree. F. to form a product mixture and thereafter recovering from the product mixture purified 2,6-naphthalenedicarboxylic acid.
    Type: Grant
    Filed: October 7, 1996
    Date of Patent: March 17, 1998
    Assignee: Amoco Corporation
    Inventors: Juergen K. Holzhauer, Rusins Albertins, Stephen V. Hoover, David L. Sikkenga
  • Patent number: 5723658
    Abstract: The present invention relates to a process for the preparation of salts of substituted or unsubstituted phthalic acids, by reacting a compound of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and are H, F, Cl, Br, CF.sub.3, OH, an alkoxy or alkyl radical in each case having 1 to 4 carbon atoms, or a radical --NR.sup.7 R.sup.8, in which R.sup.7 and R.sup.8 are identical or different and are H, an alkyl radical having 1 to 4 carbon atoms, or a phenyl radical, R.sup.5 and R.sup.6 are identical or different and are H, a --CO-- alkyl group having 1 to 6 carbon atoms in the alkyl radical, or a benzoyl group, or R.sup.5 and R.sup.6 together form a radical of the formula ##STR2## in which R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are identical or different and are H, F, Cl, Br, CF.sub.3, OH, an alkoxy or alkyl radical in each case having 1 to 4 carbon atoms, or a radical --NR.sup.7 R.sup.8, in which R.sup.7 and R.sup.
    Type: Grant
    Filed: May 2, 1996
    Date of Patent: March 3, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Theodor Papenfuhs
  • Patent number: 5679848
    Abstract: A process for the preparation of terephthalic acid (TA) from pure dimethyl terephthalate (DMT) and/or DMT intermediate product by hydrolysis in a countercurrent reactor at a conversion of greater than 99% and crystallization to give the solid product, characterized in that the sum of the stripping steam (S) and reaction water (W) satisfies the relationshipL.ltoreq.S+W.ltoreq.2L,wherein (L) represents the amount of water necessary to keep the terephthalic acid (TA) produced largely in solution during the reaction and in the bottom of the reactor, and the terephthalic acid produced is crystallized in a crystallization which is free from washing stages.
    Type: Grant
    Filed: January 18, 1996
    Date of Patent: October 21, 1997
    Assignee: Huels Aktiengesellschaft
    Inventors: Hermann-Josef Korte, Anton Schoengen, Christoph Schwarz, Thomas Jostmann
  • Patent number: 5659076
    Abstract: A process for the transesterification of dimethyl succinylsuccinate with one or more aliphatic alcohols which in each case have at least 2 C atoms, in the presence of an acidic catalyst and in the presence or absence of a diluent which is inert under the reaction conditions, with exclusion of oxygen and under pressure, at least one of the two methoxy groups being replaced by the oxy group corresponding to the alcohol used and use of the process in a process for the preparation of terephthalic acids and of quinacridones.
    Type: Grant
    Filed: August 25, 1995
    Date of Patent: August 19, 1997
    Assignee: DSM Chemie Linz GmbH
    Inventors: Franz Thomas Schwarz, Johann Altreiter, Franz Mostl
  • Patent number: 5654470
    Abstract: There is described a process for the depolymerization of polyethylene terephthalate into component monomers at ambient pressure. Monomer solids that deposit during cooling, as part of the recovery operation, are removed using a scraped wall heat exchanger.
    Type: Grant
    Filed: July 26, 1996
    Date of Patent: August 5, 1997
    Assignee: Eastman Kodak Company
    Inventors: Andrius Algimantas Naujokas, William James Gamble
  • Patent number: 5629446
    Abstract: A process for preparing purified 2,6-naphthalenedicarboxylic acid which comprises hydrolyzing a dialkyl-2,6-naphthalenedicarboxylate with water at a reaction temperature of at least about 450.degree. F. under liquid phase condition, the amount of water present being sufficient to solubilize, at the reaction temperature, at least about 10 percent of the 2,6-naphthalenedicarboxylic acid formed; and a process for purifying 2,6-naphthalenedicarboxylic acid comprising combining impure 2,6-naphthalenedicarboxylic acid with a purification solvent, heating the resulting mixture under liquid phase conditions at a temperature of at least about 500.degree. F. to form a product mixture and thereafter recovering from the product mixture purified 2,6-naphthalenedicarboxylic acid.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: May 13, 1997
    Assignee: Amoco Corporation
    Inventors: Juergen K. Holzhauer, Rusins Albertins, Stephen V. Hoover, David L. Sikkenga
  • Patent number: 5596104
    Abstract: 3,4,6-trifluorophthalic acid is prepared in high yield by reaction of a 3,4,6-trichloro-N-substituted phthalimide with potassium fluoride at temperatures in the range of 200.degree. to 270.degree. C. in the absence of a catalyst to form the corresponding trifluoro-N-substituted phthalimide which, in turn, is hydrolyzed to form the 3,4,6-trifluorophthalic acid.
    Type: Grant
    Filed: June 18, 1993
    Date of Patent: January 21, 1997
    Assignee: Occidental Chemical Corporation
    Inventors: Neil J. O'Reilly, William S. Derwin, Henry C. Lin, Deanne M. Nowak
  • Patent number: 5591877
    Abstract: Fluorinated carboxylic acids can be recovered from materials which contain them by releasing, if necessary, the carboxylic acids with sufficiently strong acids, esterifying the released acids and distilling off the esters. The esters can be advantageously directly hydrolyzed with aqueous ammonia solution to give the corresponding ammonium salts.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: January 7, 1997
    Assignee: Hoechst AG
    Inventors: Reinhold Obermeier, Gunter Stefaniak
  • Patent number: 5576456
    Abstract: There is described a process for the depolymerization of polyethylene terephthalate into component monomers using a reactor in which the polyethylene terephthalate is a discontinuous phase which contacts a continuous phase of superheated methanol vapor.
    Type: Grant
    Filed: January 22, 1996
    Date of Patent: November 19, 1996
    Assignee: Eastman Kodak Company
    Inventors: William J. Gamble, Andrius A. Naujokas
  • Patent number: 5563294
    Abstract: A process for preparing purified 2,6-naphthalenedicarboxylic acid which comprises hydrolyzing a dialkyl-2,6-naphthalenedicarboxylate with water at a reaction temperature of at least about 450.degree. F. under liquid phase condition, the amount of water present being sufficient to solubilize, at the reaction temperature, at least about 10 percent of the 2,6-naphthalenedicarboxylic acid formed; and a process for purifying 2,6-naphthalenedicarboxylic acid comprising combining impure 2,6-naphthalenedicarboxylic acid with a purification solvent, heating the resulting mixture under liquid phase conditions at a temperature of at least about 500.degree. F. to form a product mixture and thereafter recovering from the product mixture purified 2,6-naphthalenedicarboxylic acid.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: October 8, 1996
    Assignee: Amoco Corporation
    Inventors: Juergen K. Holzhauer, Rusins Albertins, Stephen V. Hoover, David L. Sikkenga