Purification Or Recovery Patents (Class 568/699)
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Patent number: 6472568Abstract: The invention relates to a process for preparing at least one aliphatic monoalcohol, generally in excess, and at least one olefin. The process is performed in a distillation and reaction device having a reaction section and a distillation-reaction section. The distillation-reaction section has a distillation zone with at least one means for circulation of the effluent from the reaction section to the distillation zone. Effluent from the reaction section is circulated to the distillation zone. The distillation-reaction section also has at least one distillation-reaction zone having at least one catalyst bed. The distillation-reaction zone is distinct from the distillation zone and provides at least partly the reflux of the distillation zone. The distillation-reaction section can also have at least one complementary reaction zone containing at least one catalyst bed.Type: GrantFiled: September 7, 2000Date of Patent: October 29, 2002Assignee: Institute Francais du PetroleInventors: Marie-Claire Marion, Alain Forestiere, Christophe Thille, Jean-Charles Viltard
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Patent number: 6458856Abstract: An improvement to the process for separating dimethyl ether (DME) from byproducts in a one-step catalytic conversion of synthesis gas (syngas), the improvement comprising using a scrubbing solvent comprising a mixture of dimethyl ether and methanol for the separation of dimethyl ether and carbon dioxide from the unconverted synthesis gas in a scrubbing column. Additional improvements include recycling of the scrubbing solution, multi-step processing of the liquid effluent from the scrubber, and methods of processing the methanol-water effluent of the flash column that is interposed between the DME reactor and the scrubber.Type: GrantFiled: November 7, 2001Date of Patent: October 1, 2002Assignee: Air Products and Chemicals, Inc.Inventors: Xiang-Dong Peng, Barry W. Diamond, Tsun-Chiu Robert Tsao, Bharat Lajjaram Bhatt
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Patent number: 6417408Abstract: The present invention provides a process for producing a (poly)alkylene glycol monoalkyl ether with high selectivity and high yield. In this process, the (poly)alkylene glycol monoalkyl ether is produced by reacting an olefin and a (poly)alkylene glycol in the presence of a catalyst, wherein: 1) a crystalline metallosilicate is used as the catalyst, and at least a portion of the used catalyst is regenerated, and the regenerated catalyst is recycled as the catalyst for the reaction; or 2) the reaction between the olefin and the (poly)alkylene glycol is carried out in the presence of either or both of a (poly)alkylene glycol dialkyl ether and an alcohol.Type: GrantFiled: February 21, 2001Date of Patent: July 9, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Yoshiyuki Onda, Masaru Kirishiki, Hideaki Tsuneki, Yukio Kadono
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Patent number: 6387222Abstract: A method of distillation for separating a material which is solid at ambient temperature from a lower boiling and lower melting point material, and the apparatus.Type: GrantFiled: March 30, 2000Date of Patent: May 14, 2002Assignee: BASF AktiengesellschaftInventors: Christian Tragut, Gerd Kaibel
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Publication number: 20020049356Abstract: A process for the purification of polyethers prepared by acid catalyzed condensation of polyhydroxy compounds includes the steps of: (a) heating the polyether with water for a time and at temperature sufficient to substantially hydrolyze esters formed during polymerization; and (b) separating the polyether from the water. The heating of the polyether and water may be conducted under reflux at a temperature of 60 to 100° C. for a period of 2 to 20 hours. The polyether recovered from step (b) may be subjected to further washing with hot water to remove residual acid.Type: ApplicationFiled: December 30, 1999Publication date: April 25, 2002Inventors: PATHIRAJA A. GUNATILLAKE, SIMON JOHN MCCARTHY, GORDON FRANCIS MEIJS
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Publication number: 20020000366Abstract: A distillation procedure is provided for the separation of impurities from organic materials such as glycols and glycol ethers whereby a liquid stripping component is interfaced into a distillation column with or below the organic material introduction, heat being provided by a reboiler, the stripping component and impurities being removed overhead.Type: ApplicationFiled: August 23, 2001Publication date: January 3, 2002Applicant: ARCO CHEMICAL TECHNOLOGY, L.P.Inventor: Vijai P. Gupta
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Patent number: 6278029Abstract: A process for eliminating at least pollutants including polar compounds present in a first fluid, with said first fluid sent to a subsequent treatment, e.g., an etherification process: a) the first fluid containing pollutants is contacted with an auxiliary fluid such as a vapor phase, under operating conditions that are selected so as to obtain, at the end of this first stage, said first fluid that is purified and freed of, for the most part, pollutants, and a vapor phase that is loaded with pollutants, said vapor phase being produced during one phase of the process, and b) at least a portion of said first purified fluid is recycled to a subsequent treatment stage.Type: GrantFiled: December 16, 1998Date of Patent: August 21, 2001Assignee: Institut Francais du PetroleInventors: Alain Forestiere, Quentin Debuisschert, Pierre Marache, Paul Mikitenko
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Patent number: 6264800Abstract: A procedure is provided for the separation of close boiling impurities from products which have slightly higher polarity than the impurities, for example, separation of di-propylene glycol di-tert-butyl ether (DE) from di-propylene glycol mono-tert-butyl ether (DPTB) by distillation, water or steam being used as stripping component with heat provided by a reboiler.Type: GrantFiled: July 19, 2000Date of Patent: July 24, 2001Assignee: Arco Chemical Technology, L.P.Inventor: Vijai P. Gupta
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Patent number: 6232509Abstract: A process for the separation and recovery of methyl tertiary butyl ether from mixed C4/C5 streams, such as resulting from the co-production of methyl tertiary butyl ether and tertiary amyl methyl ether from the reaction of methanol with isobutene and isoamylenes in a mixed C4/C5 stream. In a distillation column reactor the reaction is carried out concurrently with distillation of the products from the unreacted materials. In the distillation little or no MTBE is carried overhead with the unreacted C4's, C5's and methanol by controlling the methanol concentration in said column to maintain substantially a methanol/C5 azeotrope in the overheads.Type: GrantFiled: June 9, 2000Date of Patent: May 15, 2001Assignee: Catalytic Distillation TechnologiesInventors: Lawrence A. Smith, Jr., Henry J. Semerak, Willibrord A. Groten
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Patent number: 6232508Abstract: A process for the manufacture of ether from a feedstock containing isoolefins and linear olefins. The process is one which has a high conversion of isoolefins thereby permitting the separation of linear olefins without the associated difficulty in separating isomers.Type: GrantFiled: February 12, 1996Date of Patent: May 15, 2001Assignee: Phillips Petroleum CompanyInventors: Gary R. Patton, Robert O. Dunn
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Patent number: 6218582Abstract: A method for the preparation of methyl tertiary butyl ether is provided wherein a mixture of methanol and substantially peroxides-free tertiary butyl alcohol are catalytically reacted to form a reaction product comprising unreacted methanol, unreacted tertiary butyl alcohol, water, isobutylene and methyl tertiary butyl ether, that is separated into a substantially anhydrous first lighter distillation fraction comprising isobutylene, methanol and methyl tertiary butyl ether and a second heavier distillation fraction comprising methanol, tertiary butyl alcohol and water, and wherein the isobutylene and methanol in the first distillation fraction are reacted to form an isobutylene conversion product that contains additional methyl tertiary butyl ether that is substantially free from tertiary butyl alcohol.Type: GrantFiled: May 19, 1995Date of Patent: April 17, 2001Assignee: Huntsman International LLCInventors: Charles Joseph Kruse, Kyle Lee Preston, Brian Lawrence Benac
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Patent number: 6214172Abstract: In a process for the preparation of methylglyoxal dimethyl acetal from methylglyoxal and methanol in the presence of an acidic ion exchanger, water is introduced in an amount sufficient to form an acidic reaction mixture in which the acetal product and water form an azeotropic mixture, with or without the retention of some methanol reactant. After subjecting a single phase acidic reaction mixture to an azeotropic distillation, it will separate into two distinct liquid phases with a simple recovery of the acetal product from the aqueous phase.Type: GrantFiled: April 25, 1997Date of Patent: April 10, 2001Assignee: BASF AktiengesellschaftInventors: Carsten Gröning, Klaus Ebel, Gerd Kaibel, Jörg Therre, Jürgen Koopmann, Helmuth Menig, Gerhard Fritz, Rainer Dietz
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Patent number: 6197163Abstract: The impurity content, e.g. propionitrile, in a fraction containing C5 or C6 tertiary olefins obtained by cracking hydrocarbons is reduced by distilling with an alkanol and removing the impurity as a higher boiling point fraction.Type: GrantFiled: November 29, 1993Date of Patent: March 6, 2001Assignee: Catalytic Distillation TechnologiesInventor: Claus-Peter Thomas Hälsig
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Patent number: 6159344Abstract: The invention relates to a distillation and reaction device having a reaction section and a distillation-reaction section. The distillation-reaction section has a distillation zone with at least one device for circulation of the effluent from the reaction section to the distillation zone. Effluent from the reaction section is circulated to the distillation zone. The distillation-reaction section also has at least one distillation-reaction zone having at least one catalyst bed. The distillation-reaction zone is distinct from the distillation zone and provides at least partly the reflux of the distillation zone. The distillation-reaction section can also have at least one complementary reaction zone containing at least one catalyst bed. The invention further relates to a process for preparing at least one aliphatic monoalcohol, generally in excess, and at least one olefin.Type: GrantFiled: July 25, 1997Date of Patent: December 12, 2000Assignee: Institut Francais du PetroleInventors: Marie-Claire Marion, Alain Forestiere, Christophe Thille, Jean-Charles Viltard
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Patent number: 6107526Abstract: A catalytic distillation process for producing high purity ethyl tertiary butyl ether that contains less than 0.6 weight percent ethanol, and preferably less than 0.07 weight percent ethanol, has been developed. The high purity ethyl tertiary butyl ether is withdrawn directly from a catalytic distillation column; no downstream processing is necessary to remove excess ethanol from the ether product. A stream containing largely normal butane is generated by a C.sub.4 distillation column along with a stream containing isobutane. The stream containing isobutane is dehydrogenated to form a stream containing isobutylene. Ethanol, the stream containing isobutylene, and the stream containing largely normal butane are introduced to an etherification zone containing a catalytic distillation column. The catalytic distillation column is operated under conditions which result in the reaction of the ethanol with the isobutylene to form ethyl tertiary butyl ether.Type: GrantFiled: June 18, 1998Date of Patent: August 22, 2000Assignee: UOP LLCInventors: Stanley J. Frey, Scott P. Davis, Steven L. Krupa, Paul R. Cottrell
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Patent number: 6087539Abstract: A process for producing an ether compound represented by the general formula (II) or (III): ##STR1## wherein R.sup.1 and R.sup.2 represent each an alkyl group or a cycloalkyl group and n represents an integer of 1 to 50, which comprises bringing an acetal compound represented by the general formula (I): ##STR2## into reaction with hydrogen in the presence of a solid catalyst comprising (A) nickel in an amount corresponding to 10 to 70% by weight of metallic nickel, and (B) at least one compound selected from the group consisting of oxides of silicon, aluminum, magnesium, titanium, and zirconium; and synthetic or natural inorganic oxides containing one or more of these oxides as the constituents thereof. A vinyl ether polymer having a terminal ether group can be obtained with a good yield without causing corrosion of the apparatus used for the reaction.Type: GrantFiled: October 20, 1997Date of Patent: July 11, 2000Assignee: Idemitsu Kosan Co., Ltd.Inventors: Hirotaka Yamasaki, Akihisa Ogawa, Shigeru Kamimori, Yoshikazu Hirao, Keiji Fujita, Tokuyuki Yoshimoto
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Patent number: 6069284Abstract: A process to separate diisopropyl ether from a mixture of diisopropyl ether, isopropyl alcohol, and water has been developed. The process begins with distilling, in a distillation column, the mixture into a bottoms stream containing water and isopropyl alcohol and an overhead stream containing an azeotrope of diisopropyl ether, isopropyl alcohol, and water. The overhead stream is condensed and allowed to form an aqueous phase enriched in isopropyl alcohol and water and an organic phase enriched in diisopropyl ether with some water and isopropyl alcohol in an overhead receiver. The aqueous phase is recycled to the distillation column. The organic phase is passed to a drier to form a bottoms product stream containing at least 99 mole percent diisopropyl ether and a drier overhead stream containing an azeotrope of diisopropyl ether, isopropyl alcohol, and water.Type: GrantFiled: June 17, 1998Date of Patent: May 30, 2000Assignee: UOP LLCInventors: Charles P. Luebke, William A. Leet
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Patent number: 6037502Abstract: This invention provides an improved etherification process that reduces the amount of acidic-ion-exchange-resin catalyst that is deactivated by nitriles. This process uses a water phase to remove nitriles from a hydrocarbon phase followed by an alcohol phase to remove the nitriles from the water phase. An hydrogenation catalyst is used to convert the nitriles to amines so that they can be more easily removed from the alcohol phase.Type: GrantFiled: May 30, 1996Date of Patent: March 14, 2000Assignee: Phillips Petroleum CompanyInventors: Gary R. Patton, Robert O. Dunn, Gary A. Delzer, Marvin M. Johnson
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Patent number: 5998675Abstract: A process for preparing tertiary alkyl ethers comprises the steps of reacting C.sub.4-7 isoolefins of an olefinic hydrocarbon feedstock with an alkanol in the presence of a first catalyst in a reaction zone to form a reaction mixture containing a tertiary alkyl ether or a mixture of tertiary alkyl ethers, feeding the reaction mixture to a distillation column, distilling the reaction mixture and recovering the alkyl ether(s) with the bottoms product of the distillation. An azeotrope formed by unreacted C.sub.4 hydrocarbons and the alkanol is withdrawn as an overhead product of the distillation. According to the invention, a part of the liquid flow of the column is withdrawn to form a side drawoff, and the side drawoff is recirculated to the reaction zone. As a result, the conversion of the reactive C.sub.6 hydrocarbons is increased and the operating cost of the ethers process is reduced.Type: GrantFiled: June 22, 1998Date of Patent: December 7, 1999Assignee: Neste OyInventor: Petri Lindqvist
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Patent number: 5990361Abstract: A low pressure catalytic distillation process for producing high purity ethyl tertiary butyl ether that contains less than 0.6 weight percent ethanol, and preferably less than 0.07 weight percent ethanol, has been developed. The high purity ethyl tertiary butyl ether is withdrawn directly from a catalytic distillation column. No downstream processing is necessary to remove excess ethanol from the ether product. A stream containing a significant amount of one or more inert azeotropic agents such as normal butane, isopentane, and isobutane is introduced along with the isobutylene and ethanol reactants into an etherification zone containing a catalytic distillation column. The catalytic distillation column is operated under low pressure conditions which result in the reaction of the ethanol with the isobutylene to form ethyl tertiary butyl ether.Type: GrantFiled: June 18, 1998Date of Patent: November 23, 1999Assignee: UOP LLCInventors: Stanley J. Frey, Scott P. Davis, Steven L. Krupa, Paul R. Cottrell
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Patent number: 5985100Abstract: Butanol and dibutyl ether are separated from a mixture containing water, dibutyl ether and n-butanol, 2-butanol and/or isobutanol by a process in whicha) the mixture is introduced into a first distillation column, essentially butanol is separated off at the bottom of this distillation column and the mixture taken off at the top of the distillation columnb) is introduced into a second distillation column and essentially dibutyl ether is separated off at the bottom of this second distillation column and the mixture formed at the top of the second distillation column is removed,c) the second distillation column being operated at a higher pressure than the first distillation column and at least one of the two mixtures taken off via the top of the distillation columns being subjected to phase separation, only the organic phase separated off being fed to the second distillation column in the case of phase separation downstream of the first distillation column, and separation into an aqueous and an organic phase alsType: GrantFiled: February 17, 1998Date of Patent: November 16, 1999Assignee: BASF AktiengesellschaftInventors: Maik Aron, Harald Rust
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Patent number: 5973096Abstract: A process for purifying a polyether, which comprises adding to a polyether (A) containing a first salt, water (B) and a compound (C) which is capable of reacting with an ion constituting the first salt to form a second salt which is essentially insoluble in the polyether (A), then removing water, followed by removing the second salt from the polyether (A).Type: GrantFiled: December 16, 1997Date of Patent: October 26, 1999Assignee: Asahi Glass Company Ltd.Inventors: Takashi Watabe, Hiroshi Hatano, Kazunori Chiba, Takao Doi, Toru Ueno, Etsuko Sakai, Minoru Yamada, Shinya Saiki, Hirotsugu Yamamoto, Toshihiko Higuchi
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Patent number: 5908964Abstract: The invention concerns a process for preparing a tertiary alkyl ether product. The process comprises reacting the isoolefins of an olefinic hydrocarbon feedstock in a reaction zone (1-3) with an alkanol to form a reaction mixture, which is subjected to distillation in a first distillation zone (4). The bottoms product of the first distillation contains the ether(s), whereas the overhead stream contains unreacted alkanol and a mixture of light hydrocarbons. The overhead stream is subjected to a second distillation in a second distillation zone (15). The overhead product of the second distillation mainly contains the lightest hydrocarbons and a small amount of alkanol, and the bottoms product contains an essentially oxygenate-free hydrocarbon stream which can be used as such for alkylation. In order to increase the conversion of the process, a side drawoff is withdrawn from the second distillation zone (15) and recirculated to the reaction zone (1-3).Type: GrantFiled: February 19, 1997Date of Patent: June 1, 1999Assignee: Neste OyInventors: Matti Koskinen, Petri Lindqvist, Harri Jarvelin, Juhani Aittamaa
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Patent number: 5882485Abstract: A process for the separation of dimethyl ether and chloromethane in mixturesA process for the separation of dimethyl ether and chloromethane in mixtures by two distillation steps. In the first step, the mixture is subjected to an extractive distillation with water, aqueous salt solutions or organic liquids as extractant, the top product being chloromethane. In the second step, the dimethyl ether is separated from the extractant.Type: GrantFiled: June 23, 1997Date of Patent: March 16, 1999Assignee: Hoechst AktiengesellschaftInventors: Peter Roth, Erhard Leistner, Hans Haverkamp, Wolfgang Wendel, Michael Kleiber
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Patent number: 5847230Abstract: In an etherification process that uses an FCC effluent as a source of isoolefins, the buildup of nitrites in an alcohol-containing stream that is recycled to the etherification zone is prevented by dragging at least a portion of a water-containing stream produced by a water washing of the FCC effluent and returning the water-containing stream to the FCC gas concentration zone. As a result, the etherification catalyst deactivation rate is reduced and without increasing the net amount of fresh water employed by the process combination.Type: GrantFiled: May 20, 1997Date of Patent: December 8, 1998Assignee: UOP LLCInventors: Paul R. Cottrell, Ricardo Castillo
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Patent number: 5847224Abstract: A process for improving the color of oxygenates, such as MTBE, ETBE and TAME, which utilizes a hydrogenation treater in the presence of a catalyst, containing at least one noble metal, along with a circulation of hydrogen to remove the color. The process reduces existing color bodies in the oxygenate and may proceed at room temperature and at normal pressure for economically providing a completely clear product having a +30 saybolt number.Type: GrantFiled: June 23, 1995Date of Patent: December 8, 1998Assignee: Global Octanes CorporationInventors: Kunio Koga, Misao Mori
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Patent number: 5843286Abstract: A process for the preparation and fractionation of a mixture of dimethyl ether and chloromethane by extractive distillation with water as extractant. The mixture is prepared by reacting methanol with hydrogen chloride. It is then subjected to an extractive distillation with water as extractant, resulting in chloromethane as top product. In the next step, the dimethyl ether is removed by distillation and, in another step, the extraction water is separated from the methanol which is still present.Type: GrantFiled: June 23, 1997Date of Patent: December 1, 1998Assignee: Hoechst AktiengesellschaftInventors: Peter Roth, Erhard Leistner, Hans Haverkamp
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Patent number: 5817906Abstract: The present invention relates to a process for the production of light olefins comprising olefins having from 2 to 4 carbon atoms per molecule from a crude oxygenate feedstock. The crude oxygenate feedstock comprises an alcohol, and water. The process comprises passing the crude oxygenate feedstock to catalyst to a distillation with reaction zone to convert the alcohol to an ether and produce an ether product having a reduced water relative to the crude oxygenate feedstock and a first water stream. The ether product is passed to an oxygenate conversion zone containing a metal aluminosilicate catalyst to produce a light olefin stream.Type: GrantFiled: August 10, 1995Date of Patent: October 6, 1998Assignee: UOP LLCInventors: Terry L. Marker, Christopher David Gosling
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Patent number: 5811566Abstract: A process for purifying a polyether, which comprises adding to a polyether (A) containing a first salt, water (B) and a compound (C) which is capable of reacting with an ion constituting the first salt to form a second salt which is essentially insoluble in the polyether (A), then removing water, followed by removing the second salt from the polyether (A).Type: GrantFiled: July 17, 1995Date of Patent: September 22, 1998Assignee: Asahi Glass Company Ltd.Inventors: Takashi Watabe, Hiroshi Hatano, Kazunori Chiba, Takao Doi, Toru Ueno, Etsuko Sakai, Minoru Yamada, Shinya Saiki, Hirotsugu Yamamoto, Toshihiko Higuchi
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Patent number: 5811597Abstract: Methyl tertiary butyl ether is prepared from contaminated TBA by reactively distilling the contaminated TBA in a reactive distillation column to provide a lower boiling isobutylene fraction and a higher boiling aqueous TBA fraction, by distilling the higher boiling aqueous TBA fraction to provide a lower boiling TBA fraction, by charging the lower boiling isobutylene fraction, the lower boiling tertiary butyl alcohol fraction and methanol to an etherification reactor to form an etherification reaction product, by distilling the etherification reaction product to provide a lower boiling fraction containing isobutylene, methanol and methyl tertiary butyl ether by charging the lower boiling fraction to a finishing reactor to react the isobutylene and methanol contained therein to from additional MTBE and by recovering MTBE from the etherification reaction product and the isobutylene conversion product.Type: GrantFiled: August 26, 1996Date of Patent: September 22, 1998Assignee: Huntsman Specialty Chemicals Corp.Inventors: Rei-Yu Judy Hwan, Mark Elliott Taylor, John Frederick Knifton, Melvin Ernest Stockton, John Ronald Sanderson
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Patent number: 5792899Abstract: A process for the management of polynuclear aromatic compounds produced in a hydrocarbon dehydrogenation zone wherein the effluent from the hydrocarbon dehydrogenation zone is contacted with an adsorbent to reduce the concentration of polynuclear aromatic compounds. The resulting dehydrogenated hydrocarbon having a reduced concentration of polynuclear aromatic compounds is reacted with methanol to produce an ether. A portion of the ether is contacted with a spent bed of adsorbent to recover at least a portion of the polynuclear aromatic compounds adsorbed thereon to thereby regenerate the adsorbent.Type: GrantFiled: September 27, 1996Date of Patent: August 11, 1998Assignee: UOP LLCInventor: Paul R. Cottrell
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Patent number: 5763685Abstract: MTBE is prepared from TBA and MeOH by passing a feed mixture comprising TBA and MeOH through a primary MTBE reaction zone to form a primary reaction product containing MTBE, unreacted TBA, unreacted MeOH, isobutylene and water; the primary reaction product is fractionated to provide a first lighter distillation fraction comprising isobutylene, MeOH and MTBE and a first higher boiling distillation fraction comprising MeOH, TBA and water and the first higher boiling distillation fraction is charged to a second stage MTBE reaction zone to form a second stage reaction product comprising unreacted MeOH, unreacted TBA water, isobutylene and MTBE.Type: GrantFiled: August 17, 1995Date of Patent: June 9, 1998Assignee: Huntsman Specialty Chemicals CorporationInventors: Charles Joseph Kruse, Kyle Lee Preston, Brian Lawrence Benac
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Patent number: 5750799Abstract: A process for production and recovery of dimethyl ether by dehydration of methanol which significantly reduces the distillation duties associated to the preparation of the fresh methanol feed stock and/or the recovery of unconverted methanol for use as recycle feed stock to the dimethyl ether production process while maintaining a high rate of conversion of methanol to dimethyl ether.Type: GrantFiled: March 15, 1995Date of Patent: May 12, 1998Assignee: Starchem, Inc.Inventor: Christiaan P. van Dijk
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Patent number: 5741952Abstract: An MTBE recycle stream (which consists mainly of TBA and methanol) contaminated with residual amounts of tertiary butyl hydroperoxide, ditertiary butyl peroxide and allyl tertiary butyl peroxide can be effectively catalytically treated under mild conversion conditions with a silica-supported nickel, copper, chromium, iron catalyst in order to substantially completely decompose the peroxide contaminants and to thereby provide a treated MTBE recycle stream which is not only substantially free from contaminating quantities of such peroxides, but which also contains an enhanced amount of methyl tertiary butyl ether.Type: GrantFiled: January 11, 1993Date of Patent: April 21, 1998Assignee: Huntsman Specialty Chemicals CorporationInventors: John Ronald Sanderson, John Frederick Knifton
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Patent number: 5741951Abstract: Methyl tertiary butyl ether and diisobutylene are prepared by reacting methanol with tertiary butyl alcohol to provide an etherification reaction product containing methyl tertiary butyl ether, tertiary butyl alcohol, methanol, isobutylene, and water. A methyl tertiary butyl ether product fraction and an isobutylene fraction are recovered from the etherification reaction product; the isobutylene fraction is charged to an isobutylene conversion reaction zone to form a diisobutylene conversion product, and the diisobutylene conversion product is charged to a diisobutylene distillation zone and separated therein into a lower boiling distillation fraction comprising isobutylene, and diisobutylene and a higher boiling distillation fraction consisting essentially of diisobutylene.Type: GrantFiled: December 30, 1996Date of Patent: April 21, 1998Assignee: Huntsman Specialty Chemicals CorporationInventor: Kyle Lee Preston
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Patent number: 5741953Abstract: An aqueous methanol feed stream contaminated with tertiary butyl alcohol is charged to a reactive distillation column having a reaction distillation section in the upper portion thereof containing an acid cation exchange resin and separated therein into a substantially anhydrous lower boiling methanol fraction contaminated with isobutylene and a higher boiling water fraction by charging the feed stream to the lower portion of the reactive distillation column to separate the feed stream into a higher boiling water fraction and a lower boiling methanol fraction containing a tertiary butyl alcohol-water azeotrope for upward flow into the reactive distillation section for reaction of the tertiary butyl alcohol to form isobutylene, MTBE and water and recovery of a substantially anhydrous lower boiling methanol fraction contaminated with isobutylene and MTBE.Type: GrantFiled: August 17, 1995Date of Patent: April 21, 1998Assignee: Huntsman Specialty Chemicals CorporationInventor: Kyle Lee Preston
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Patent number: 5723698Abstract: Disclosed is a method for decomposing formate esters, free acids and peroxides in a tertiary butyl alcohol stream to produce noncondensible gas products which comprises reacting said tertiary butyl alcohol stream or a methyl tertiary butyl alcohol stream containing formate esters over a catalyst comprising a non-noble Group VIII metal and a metal of Group IB on a support comprising an inert composition mixed with a hydrotalcite-like composition.Type: GrantFiled: December 18, 1995Date of Patent: March 3, 1998Assignee: Huntsman Specialty Chemicals CorporationInventors: Pei-Shing Eugene Dai, Laurence Darrel Neff, Kyle Lee Preston, Rei-Yu Judy Hwan
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Patent number: 5705712Abstract: A highly integrated process for concurrently producing diisopropyl ether and an isopropyl tertiary alkyl ether has been developed. Optionally, high purity isopropyl alcohol may also be collected as a product. In a first reactor, propylene and water are reacted to form isopropyl alcohol, a portion of which is further reacted to form diisopropyl ether. After removing unreacted propylene, the effluent of the first reactor is separated into an ether rich stream, a water rich stream and an alcohol rich stream. The alcohol rich stream is dried to provide dry isopropyl alcohol. A portion of the dry isopropyl alcohol may be removed and collected as a product. A portion of the dry isopropyl alcohol and isobutylene, isoamylene or a mixture thereof are reacted to form an isopropyl tertiary alkyl ether in a second reactor. Unreacted iso-olefins and inert compounds are then removed from the second reactor effluent.Type: GrantFiled: October 5, 1995Date of Patent: January 6, 1998Assignee: UOPInventors: Stanley J. Frey, Robert J. Schmidt, Terry L. Marker, Richard E. Marinangeli
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Patent number: 5705711Abstract: Tertiary butyl alcohol and methanol are reacted in a primary reactor in the presence of an acid cation exchange resin to provide a primary reaction product comprising methyl tertiary butyl ether, unreacted tertiary butyl alcohol, unreacted methanol, isobutylene, water and oxygen-containing by-products, and the primary reaction product is charged to a reactive distillation column where additional methyl tertiary butyl ether is prepared from the methanol, tertiary butyl alcohol and isobutylene present in the primary reaction product.Type: GrantFiled: August 17, 1995Date of Patent: January 6, 1998Assignee: Huntsman Specialty Chemicals CorporationInventor: Kyle Lee Preston
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Patent number: 5698747Abstract: Ethers, for example those produced by acid-catalyzed dehydration of alcohols, are freed from esters by treatment with an alkoxide, and are especially suitable as drilling fluid components.Type: GrantFiled: April 12, 1994Date of Patent: December 16, 1997Assignee: Exxon Chemical Patents Inc.Inventors: Allen David Godwin, Georges Marie Karel Mathys
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Patent number: 5684212Abstract: This invention provides a process to remove nitriles. This invention also provides an improved etherification process that reduces the amount of acidic-ion-exchange-resin catalyst that is deactivated by nitriles. These processes use a water phase to remove nitriles from a hydrocarbon phase followed by a steam, or fuel gas, phase to remove the nitriles from the water phase.Type: GrantFiled: May 30, 1996Date of Patent: November 4, 1997Assignee: Phillips Petroleum CompanyInventors: Gary R. Patton, Robert O. Dunn
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Patent number: 5684213Abstract: A method for producing dialkyl ethers comprising feeding a stream containing a C.sub.1 to C.sub.4 alcohol to a distillation column reactor into a feed zone, contacting the stream with a fixed bed zeolite prepared as a distillation structure to form the corresponding dialkyl ether and water, and concurrently fractionating the ether product from the water and unreacted materials wherein the improvement is the addition of a small amount of hydrogen to the reaction zone to inhibit catalyst fouling and substantially increasing the catalyst life and activity.Type: GrantFiled: March 25, 1996Date of Patent: November 4, 1997Assignee: Chemical Research & Licensing CompanyInventors: Speros Peter Nemphos, Dennis Hearn
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Patent number: 5679872Abstract: A process for the separation of a mixture of an ether, an alcohol and of hydrocarbons is described in which the mixture to be separated is introduced into a first distillation column from which almost all of the hydrocarbons are recovered overhead and the purified ether is recovered from the bottom; at least one phase is extracted as a side stream from the first distillation column and sent to a second distillation column from which the alcohol is recovered from the bottom and a mixture of alcohol, ether and hydrocarbons is recovered overhead and recycled to the first distillation column. This process is of particular use in separating mixtures of ethyl tertio-butyl ether (ETBE), ethanol and C.sub.4 hydrocarbons.Type: GrantFiled: May 4, 1995Date of Patent: October 21, 1997Assignee: Institut Francais du PetroleInventor: Christian Streicher
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Patent number: 5672772Abstract: A process is disclosed for improving catalyst performance and yields in the manufacture of motor gasoline components. More particularly the process is directed to the removal of trace amounts of acetonitrile or acetone or propionitrile from a hydrocarbon feedstock such as a C.sub.4 -C.sub.6 product fraction from a fluid catalytic cracking unit, which may be used subsequently in an etherification process for the production of ethers such as MTBE and TAME. The hydrocarbon feedstock is passed to a water wash zone for the removal of the trace amounts of acetonitrile or acetone or propionitrile and the spent water comprising the nitriles is contacted with a nitrile-lean stream to regenerate the wash water. A portion of the spent water stream is withdrawn to reduce the nitrile level in the nitrile-lean water stream.Type: GrantFiled: April 10, 1996Date of Patent: September 30, 1997Assignee: UOPInventors: Stanley J. Frey, Paul R. Cottrell, David A. Hamm
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Patent number: 5671153Abstract: In a process for manufacture of a chemical product in which a plurality of individual reactant containing feedstreams are combined to form a mixed feedstream for a reactor, and wherein at least one of the plurality of feedstreams is subject to variations in reactant concentration, and another one of the plurality of feedstreams is essentially stable in reactant concentration, a desired ratio of relative reactant concentrations in the mixed feedstream is maintained by a control system which infers a reactant concentration ratio in the mixed feedstream based on process measurements and feed parameters related to the plurality of feedstock containing streams prior to their being combined. In use, flow rate of the feedstream which is essentially stable in reactant concentration is manipulated to maintain the inferred reactant concentrations in the mixed stream.Type: GrantFiled: February 24, 1995Date of Patent: September 23, 1997Assignee: Phillips Petroleum CompanyInventors: Francis M. Brinkmeyer, Steven D. Bridges, Ronald E. Miranda, Mike L. Facker
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Patent number: 5663454Abstract: Methanol and isobutylene are reacted to form a methyl tertiary butyl ether product stream containing contaminating quantities of dimethyl ether, methanol and isobutylene that is separated into a first fraction comprising isobutylene and methyl tertiary butyl ether and a second fraction comprising residual methyl tertiary butyl ether, methanol, dimethyl ether and water. The second fraction is separated into a first lower boiling distillation fraction comprising methyl tertiary butyl ether, methanol, isobutylene, dimethyl ether, and water and a first higher boiling distillation fraction comprising methanol and water. Dimethyl ether and isobutylene are recovered from the first lower boiling distillation fraction and charged to a second distillation column for separation into a second lower boiling distillation fraction consisting essentially of dimethyl ether and a second higher boiling distillation fraction comprising dimethyl ether and isobutylene.Type: GrantFiled: August 8, 1995Date of Patent: September 2, 1997Assignee: Huntsman Specialty Chemicals CorporationInventor: Kyle Lee Preston
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Patent number: 5659091Abstract: An impure methyl tertiary butyl ether product contaminated with isobutylene, methanol and water is purified by continuous counter-current contact with water and an isobutylene fraction in an extraction zone comprising a counter-current contact tower to provide an overhead raffinate comprising isobutylene, methyl tertiary butyl ether and a minor amount of water and an extract comprising methanol, water and a minor amount of methyl tertiary butyl ether; the overhead raffinate being separated in a methyl tertiary butyl ether purification distillation zone into a lighter distillation fraction comprising isobutylene and water and a heavier distillation fraction consisting essentially of methyl tertiary butyl ether; the lighter distillation fraction being decanted to remove water and to provide a distillate isobutylene fraction that is returned to the contact tower as the isobutylene fraction.Type: GrantFiled: January 17, 1995Date of Patent: August 19, 1997Assignee: Texaco Chemical Inc.Inventors: Michael Warren Peters, Yu-Hwa Edward Sheu
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Patent number: 5648499Abstract: A safe and reliable method of decomposing halogenated aromatic compounds, wherein a heat-resistant alkaline polar solvent containing halogenated aromatic compounds is contacted with a alkali at a temperature ranging from about 100.degree. C. to 300.degree. C. in order to decompose the halogenated aromatic compounds. The used solvent is removed of solid contents of salts, alkalis and the like, whereby it can be recycled.Type: GrantFiled: March 23, 1995Date of Patent: July 15, 1997Assignees: Mitsui & Co., Ltd., Neos Co., Ltd, Research Institute for Production DevelopmentInventors: Fumio Tanimoto, Tsuneo Yano
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Patent number: 5639355Abstract: A tertiary butyl hydroperoxide reaction product is distilled to provide a tertiary butyl alcohol distillation fraction containing tertiary butyl alcohol and a heavier fraction containing unreacted tertiary butyl hydroperoxide, and reaction by-products boiling below tertiary butyl alcohol, the tertiary butyl alcohol fraction is charged to a vacuum distillation column for separation into a vaporized overhead tertiary butyl alcohol fraction that is cooled to obtain a liquefaction product containing a minor amount of vaporized tertiary butyl alcohol and a major amount of a liquified tertiary butyl alcohol, andthe tertiary butyl alcohol vapors are dissolved in water to form an aqueous solution of tertiary butyl alcohol from which the tertiary butyl alcohol is recovered.Type: GrantFiled: March 13, 1995Date of Patent: June 17, 1997Assignee: Texaco Chemical Inc.Inventor: Huibert Sybrandus Jongenburger
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Patent number: 5621150Abstract: The present invention relates to a cyclic process for the preparation of ethyl tert.-alkyl ethers by the reaction of an alcohol, such as ethanol, with an iso-olefin such as isobutylene or isoamylene wherein an effluent from the reaction zone is first separated in a distillation column to provide an overhead effluent stream and a bottoms effluent stream comprising ethyl tert.-alkyl ether and unreacted ethanol, and the ether product is passed to an adsorption zone to remove the unreacted ethanol. When the reaction occurs in the presence of water, a tert. alcohol (e.g., TBA or TAA) is produced and, if returned to the reaction zone, the tertiary alcohol builds up in the process and reduces efficiency.Type: GrantFiled: April 26, 1995Date of Patent: April 15, 1997Assignee: UOPInventors: Henry Rastelli, Carmen M. Yon, Stanley J. Frey