Preparing By Reacting An Olefin And An Organic Hydroxy Containing Compound (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/697)
  • Publication number: 20010007047
    Abstract: 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: Application
    Filed: February 21, 2001
    Publication date: July 5, 2001
    Applicant: Nippon Shokubai Co., Ltd.
    Inventors: Yoshiyuki Onda, Masaru Kirishiki, Hideaki Tsuneki, Yukio Kadono
  • Patent number: 6232508
    Abstract: 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: Grant
    Filed: February 12, 1996
    Date of Patent: May 15, 2001
    Assignee: Phillips Petroleum Company
    Inventors: Gary R. Patton, Robert O. Dunn
  • Patent number: 6232509
    Abstract: 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: Grant
    Filed: June 9, 2000
    Date of Patent: May 15, 2001
    Assignee: Catalytic Distillation Technologies
    Inventors: Lawrence A. Smith, Jr., Henry J. Semerak, Willibrord A. Groten
  • Patent number: 6218582
    Abstract: 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: Grant
    Filed: May 19, 1995
    Date of Patent: April 17, 2001
    Assignee: Huntsman International LLC
    Inventors: Charles Joseph Kruse, Kyle Lee Preston, Brian Lawrence Benac
  • Patent number: 6207845
    Abstract: An aluminum compounds represented by the following general formula (1): Al(R1—SO3)1(R2)m(R3)n   (1) wherein R1 is a hydrocarbon group which may be substituted, R2 is a hydrocarbon group which may be substituted, an aliphatic hydrocarbonoxy group which may be substituted, or a halogen atom, R3 is an aromatic hydrocarbonoxy group which may be substituted, and 1, m and n are independently a number of 0 to 3, with the proviso that 1+m+n equals 3, and 1 is not 0, an acid catalyst comprising the aluminum compound, and a process for producing an ester, acetal, ketal, ether or alkyl glycoside making use of the catalyst. The catalyst is suitable for use in a variety of acid-catalyzed reactions of alcohols, i.e., reactions with carbonyl compounds, such as esterification, transesterification, acetalization and ketalization, etherification, ring-opening reactions of epoxy compounds, etc.
    Type: Grant
    Filed: November 1, 1999
    Date of Patent: March 27, 2001
    Assignee: Kao Corporation
    Inventors: Munehisa Okutsu, Tomohito Kitsuki, Katsumi Kita
  • Patent number: 6197163
    Abstract: 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: Grant
    Filed: November 29, 1993
    Date of Patent: March 6, 2001
    Assignee: Catalytic Distillation Technologies
    Inventor: Claus-Peter Thomas Hälsig
  • Patent number: 6159344
    Abstract: 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: Grant
    Filed: July 25, 1997
    Date of Patent: December 12, 2000
    Assignee: Institut Francais du Petrole
    Inventors: Marie-Claire Marion, Alain Forestiere, Christophe Thille, Jean-Charles Viltard
  • Patent number: 6156947
    Abstract: A simplified process for jointly producing butene-1 and ether in a catalytic distillation column which comprises an upper catalytic zone for etherification and a lower catalytic zone for isomerization of C.sub.4 plus olefins and conversion of butadiene. The process is especially useful when combined with a process for the production of light olefins including ethylene and propylene from methanol. According to the invention, the produced butene-1 stream is combined with ethylene to produce polyethylene.
    Type: Grant
    Filed: June 28, 1999
    Date of Patent: December 5, 2000
    Assignee: UOP LLC
    Inventor: Bipin V. Vora
  • Patent number: 6149879
    Abstract: The invention relates to a modular device that comprises a reaction zone that includes a catalyst bed and a zone for separation by distillation, as well as independent circulation channels for liquid fluid and gaseous fluid.
    Type: Grant
    Filed: February 12, 1998
    Date of Patent: November 21, 2000
    Assignee: Institut Francais du Petrole
    Inventors: Alain Forestiere, Quentin Debuisschert, Isabelle Harter, Jean-Paul Dessapt, Pierre Marache
  • Patent number: 6143936
    Abstract: A process for producing an ether and an olefin from a hydrocarbon cut containing at least one tertiary olefin, comprises synthesis of at least one tertiary alkyl ether then fractionation to obtain an organic fraction (E1) which is enriched in the tertiary alkyl ether which is decomposed into a product containing at least one alcohol and at least one tertiary olefin, which is purified in a water washing extraction zone (L1) to obtain an aqueous fraction (A1) containing the major portion of the alcohol and a fraction (B1) containing the major portion of the tertiary olefin, at least a portion of fraction (B1) being sent to a separation zone (Co1) from which an aqueous liquid fraction (La1) and a liquid fraction (Lb1) containing the major portion of the tertiary olefin are recovered.
    Type: Grant
    Filed: April 1, 1998
    Date of Patent: November 7, 2000
    Assignee: Institut Francais du Petrole
    Inventors: Marie-Claire Marion, Vincent Coupard, Alain Forestiere, Philippe Travers, Jean-Charles Viltard
  • Patent number: 6107526
    Abstract: 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: Grant
    Filed: June 18, 1998
    Date of Patent: August 22, 2000
    Assignee: UOP LLC
    Inventors: Stanley J. Frey, Scott P. Davis, Steven L. Krupa, Paul R. Cottrell
  • Patent number: 6069284
    Abstract: 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: Grant
    Filed: June 17, 1998
    Date of Patent: May 30, 2000
    Assignee: UOP LLC
    Inventors: Charles P. Luebke, William A. Leet
  • Patent number: 6049020
    Abstract: A process for producing an ether and an olefin from a hydrocarbon cut containing at least one tertiary olefin, by synthesis of at least one tertiary alkyl ether then fractionation to recover an organic fraction containing the ether which is decomposed into a product (P1) containing at least one alcohol and at least one tertiary olefin, which is fractionated, then the tertiary olefin is purified in a water washing extraction zone (L1) from which a fraction containing the tertiary olefin is recovered and sent to a separation zone (Co) from which an aqueous liquid fraction and a liquid hydrocarbon fraction containing the major portion of the tertiary olefin are recovered.
    Type: Grant
    Filed: April 1, 1998
    Date of Patent: April 11, 2000
    Assignee: Institut Francais du Petrole
    Inventors: Marie-Claire Marion, Vincent Coupard, Alain Forestiere, Philippe Travers, Jean-Charles Viltard
  • Patent number: 6049012
    Abstract: A catalyst for production of alkyl tert alkyl ether from sulfur contaminated feedstock includes an ion exchange resin; a palladium first metal phase supported on the resin; and a sulfur inhibiting second metal phase supported on the resin for inhibiting sulfur deactivation of the first metal phase, wherein the first metal phase is present at an atomic ratio to the second metal phase of between about 1:20 to about 1:0.1. A process for producing alkyl tert alkyl ethers includes the steps of providing a liquid olefinic hydrocarbon feedstock containing sulfur and having a total sulfur content of up to about 300 ppm; providing a catalyst as described above; mixing the feedstock with alcohol and hydrogen to obtain a reaction feedstock; and contacting the reaction feedstock with the catalyst under etherification conditions so as to produce alkyl tert alkyl ether.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: April 11, 2000
    Assignee: Intevep, S.A.
    Inventors: Magdalena Ramirez de Agudelo, Trino J. Romero, Emilia Mujica
  • Patent number: 6037502
    Abstract: 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: Grant
    Filed: May 30, 1996
    Date of Patent: March 14, 2000
    Assignee: Phillips Petroleum Company
    Inventors: Gary R. Patton, Robert O. Dunn, Gary A. Delzer, Marvin M. Johnson
  • Patent number: 6023002
    Abstract: Described is a reaction of a fluorinated alkoxide with an alkyl fluorovinylalkyl ether, the alkyl fluorovinylalkyl ether having alpha-beta carbon-carbon unsaturation relative to the ether oxygen, to produce a hydrofluoroether.
    Type: Grant
    Filed: January 26, 1998
    Date of Patent: February 8, 2000
    Assignee: 3M Innovative Properties Company
    Inventors: Frederick E. Behr, Yuri Cheburkov
  • Patent number: 6017371
    Abstract: A composition and method for producing a multiple boiling point ether gasoline component is provided. A mixed alcohol composition including predominantly C.sub.1 -C.sub.3 alcohols is reacted with an alkene stream to produce a mixture of ethers having different boiling points. The ether mixture is useful, when blended with gasoline, to increase oxygenation and overall motor fuel performance.
    Type: Grant
    Filed: August 5, 1993
    Date of Patent: January 25, 2000
    Assignee: NRG Technologies, Inc.
    Inventors: Jean-Louis G. Gheysens, William J. Wells, III, Richard E. Woodling
  • Patent number: 6005150
    Abstract: A simplified process for jointly producing butene-1 and ether in a catalytic distillation zone which comprises an upper catalytic zone for etherification and a lower catalytic zone for isomerization of C.sub.4 plus olefins. The process is especially usefull when combined with a process for the production of light olefins including ethylene and propylene from methanol. According to the invention, the produced butene-1 stream is combined with ethylene to produce polyethylene.
    Type: Grant
    Filed: June 22, 1998
    Date of Patent: December 21, 1999
    Assignee: UOP LLC
    Inventor: Bipin V. Vora
  • Patent number: 5998675
    Abstract: 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: Grant
    Filed: June 22, 1998
    Date of Patent: December 7, 1999
    Assignee: Neste Oy
    Inventor: Petri Lindqvist
  • Patent number: 5990361
    Abstract: 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: Grant
    Filed: June 18, 1998
    Date of Patent: November 23, 1999
    Assignee: UOP LLC
    Inventors: Stanley J. Frey, Scott P. Davis, Steven L. Krupa, Paul R. Cottrell
  • Patent number: 5981818
    Abstract: A novel process is provided which integrates the cracking of hydrocarbon containing feedstocks with the olefins purification and olefins derivative process utilizing dilute olefin feedstocks.
    Type: Grant
    Filed: October 18, 1996
    Date of Patent: November 9, 1999
    Assignee: Stone & Webster Engineering Corp.
    Inventors: David Purvis, Richard H. Mc Cue
  • Patent number: 5962750
    Abstract: A process for treating a feedstock containing olefins of 6 carbon atoms per molecule, said olefins being either potentially etherifiable or (directly) etherifiable, wherein isomerization of a portion of the potentially etherifiable olefins is accomplished in part in an isomerization zone, in the presence of an isomerization catalyst that makes it possible to obtain an isomerization effluent which comprises in part etherifiable olefins, and in that, in part, etherification is carried out, in the presence of an etherification catalyst and at least one alcohol that has 1 to 4 carbon atoms per molecule, of a portion of etherifiable olefins that are contained in the feedstock, in a first etherification zone, and in part etherification is carried out of a portion of etherifiable olefins that are contained in said isomerization effluent, in a second etherification zone, in the presence of an etherification catalyst and at least one alcohol that has 1 to 4 carbon atoms per molecule, to optimize the production of ethe
    Type: Grant
    Filed: February 15, 1996
    Date of Patent: October 5, 1999
    Assignee: Institut Francais Du Petrole
    Inventors: Charles Cameron, Alain Forestiere, Marie-Claire Marion, Jean-Luc Nocca, Jean-Luc Duplan
  • Patent number: 5914430
    Abstract: Ether compounds, which are useful as solvents, cosmetics, detergents, lubricants, emulsifiers and so on, are produced by reacting (a) a hydroxy compound with a carbonyl compound of (b) a carbonyl compound under hydrogen atmosphere in the presence of a catalyst with ease and at a low cost. The reaction is carried out while removing out produced water by using a dehydrating agent during the reaction; by distilling off the water by azeotropic dehydration and the like; or by blowing gases such as hydrogen gas to flow through the reaction system.
    Type: Grant
    Filed: July 5, 1996
    Date of Patent: June 22, 1999
    Assignee: Kao Corporation
    Inventors: Yasuyuki Fujii, Hisakazu Furugaki, Katsumi Kita, Mitsuru Uno, Eiko Tamura, Hiromasa Matsumoto
  • Patent number: 5912191
    Abstract: A process for the coupled production of alkyl tert-butyl ethers and butene oligomers from a mixture containing isobutane and n-butane. The isobutane is converted to the alkyl tert-butyl ether and the n-butane is converted to the oligomers. The ratio of the two reaction products may be controlled by setting the ratio of n-butane to isobutane appropriately by isomerization.
    Type: Grant
    Filed: July 24, 1997
    Date of Patent: June 15, 1999
    Assignee: Huels Aktiengesellschaft
    Inventors: Franz Nierlich, Paul Olbrich, Wilhelm Droste, Richard Mueller, Walter Toetsch
  • Patent number: 5908964
    Abstract: 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: Grant
    Filed: February 19, 1997
    Date of Patent: June 1, 1999
    Assignee: Neste Oy
    Inventors: Matti Koskinen, Petri Lindqvist, Harri Jarvelin, Juhani Aittamaa
  • Patent number: 5866388
    Abstract: In the field of bringing fluids into contact with solid materials, the invention relates to the use of a container which is suitable for granular materials.The container, of a material which is permeable to gases and liquids, is of substantially tetrahedral shape.
    Type: Grant
    Filed: July 9, 1992
    Date of Patent: February 2, 1999
    Inventor: Jacques Raphael Benzaria
  • Patent number: 5864052
    Abstract: The invention relates to a process for preparing di-n-butene and alkyl tertbutyl ethers in a coupled production from field butanes, which indicates (a) separating the field butanes 1 into n-butane and isobutane in the separation stage 4, (b) dehydrogenating the n-butane 5 in a dehydrogenation stage 6 to give an n-butene-containing dehydrogenation mixture 7, oligomerizing the n-butene in the oligomerization stage 10 to give an oligomer mixture 11 and separating di-n-butene 12 off from this, and (c) de-hydrogenating the isobutane 15 in the dehydrogenation stage 16 to give an isobutene-containing dehydrogenation mixture 17 and reacting the isobutene with an alkanol 20 in the etherification stage 19 to give an alkyl tert-butyl ether 21.
    Type: Grant
    Filed: July 24, 1997
    Date of Patent: January 26, 1999
    Assignee: Huels Aktiengesellschaft
    Inventors: Franz Nierlich, Paul Olbrich, Wilhelm Droste, Richard Mueller, Walter Toetsch
  • Patent number: 5852220
    Abstract: A process for producing tertiary alkyl ethers by reacting an olefinic hydrocarbon feedstock, which contains a mixture of reactive C.sub.4 -C.sub.7 isoolefins, with an alkanol in the presence of a catalyst that will enhance the reaction between the isoolefins and the alkanol. By adjusting the weight ratio of the isobutylene to the reactive C.sub.6 isoolefins of the feed to a value of about 0.2 to 10, it is possible to increase the conversion of reactive C.sub.4 's to over 95%, of reactive C.sub.5 's to over 85% and of reactive C.sub.6 's to over 57%.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: December 22, 1998
    Assignee: Neste Oy
    Inventors: Harri Jarvelin, Petri Lindqvist, Esa Tamminen
  • Patent number: 5849975
    Abstract: A process for skeletal isomerization of light normal C.sub.4-6 olefins to iso-olefins by contacting a hydrocarbon stream containing C.sub.4-6 normal olefins under isomerization conditions with a SSZ-32 zeolite catalyst.
    Type: Grant
    Filed: January 7, 1997
    Date of Patent: December 15, 1998
    Assignee: Chevron U.S.A. Inc.
    Inventors: Harris E. Kluksdahl, Lawrence W. Jossens, Thomas V. Harris, Stacey I. Zones
  • Patent number: 5811597
    Abstract: 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: Grant
    Filed: August 26, 1996
    Date of Patent: September 22, 1998
    Assignee: Huntsman Specialty Chemicals Corp.
    Inventors: Rei-Yu Judy Hwan, Mark Elliott Taylor, John Frederick Knifton, Melvin Ernest Stockton, John Ronald Sanderson
  • Patent number: 5801293
    Abstract: The invention includes a method for skeletal isomerization of C.sub.4-5 olefins. The method includes contacting in a FCC zone, at FCC conditions, an n-C.sub.4-5 olefins-containing etherification zone raffinate, with an FCC catalyst, where at least a portion of the n-C.sub.4-5 olefins in the n-C.sub.4-5 olefins-containing etherification zone raffinate are converted to iso-C.sub.4-5 olefins.
    Type: Grant
    Filed: January 10, 1997
    Date of Patent: September 1, 1998
    Assignee: Chevron U.S.A. Inc.
    Inventor: Stephen J. Miller
  • Patent number: 5792899
    Abstract: 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: Grant
    Filed: September 27, 1996
    Date of Patent: August 11, 1998
    Assignee: UOP LLC
    Inventor: Paul R. Cottrell
  • Patent number: 5792891
    Abstract: An alkene skeletal isomerization process is employed in an integrated process for the production of tertiary ether, e.g., tertiary amyl methyl ether (TAME) from the reaction of isoamylenes (iC.sub.5.sup.= 's) with methanol in the presence of an acid cation exchange resin. A light naphtha from a fluid catalytic cracking unit is used as the source of the iC.sub.5.sup.= 's in a process which separates the C.sub.5 containing fraction from the light naphtha, selectively hydrogenates the di-olefins contained in the C.sub.5 containing fraction, reacts the iC.sub.5.sup.= 's contained in the C.sub.5 containing fraction with methanol to form TAME, separates the TAME from the unreacted materials as a product, separates methanol from the unreacted materials, isomerizes a portion of the nC.sub.5.sup.= 's to iC.sub.5.sup.= 's , for example using a zeolite or an alumina treated with methanol, and use of the isomerization product as feed for a TAME reactor.
    Type: Grant
    Filed: February 3, 1997
    Date of Patent: August 11, 1998
    Assignee: Catalytic Distillation Technologies
    Inventors: John R. Adams, Lawrence A. Smith, Jr., Dennis Hearn, Edward M. Jones, Jr., Robert P. Arganbright
  • Patent number: 5792890
    Abstract: A tertiary butyl alcohol charge stock contaminated with from about 0.5 to about 2 wt. % of corrosive oxygen-containing impurities, including peroxides and formates, is passed through an oxygenates decomposition reactor containing a bed of a basic zeolite catalyst to decompose the peroxides and oxygen-containing impurities, including peroxides and formates, and to dehydrate a portion of the tertiary butyl alcohol to form isobutylene and water to form a substantially less-corrosive tertiary butyl alcohol feedstock that is substantially free from oxygen-containing impurities, including formates that is suitable for reaction with methanol in a methyl tertiary butyl ether etherification reactor to form a methyl tertiary butyl ether etherification reaction product from which methyl tertiary butyl ether can be recovered.
    Type: Grant
    Filed: February 3, 1997
    Date of Patent: August 11, 1998
    Assignee: Huntsman Specialty Chemicals Corp.
    Inventors: Pei-Shing Eugene Dai, Laurence Darrel Neff, Kyle Lee Preston, Rei-Yu Judy Hwan, John Frederick Knifton
  • Patent number: 5789627
    Abstract: Methyl tertiary butyl ether is prepared from contaminated tertiary butyl alcohol and methanol by decomposing peroxides in a peroxides decomposition reactor, by dehydrating the tertiary butyl alcohol to form isobutylene and also decomposing acidic contaminants in a tertiary butyl alcohol dehydration reactor to form a feedstock that is distilled to provide a first lower boiling fraction comprising isobutylene and water; from which isobutylene is recovered for reaction with methanol in an etherification reactor containing a bed of an etherification catalyst to form methyl tertiary butyl ether.
    Type: Grant
    Filed: February 20, 1997
    Date of Patent: August 4, 1998
    Assignee: Huntsman Specialty Chemicals Corp.
    Inventors: Rei-Yu Judy Hwan, Kyle Lee Preston
  • Patent number: 5780688
    Abstract: The invention concerns a supported catalyst in the form of packing and constructed on an open-pore support material on whose external and internal surfaces a macro-porous ion exchange resin is mechanically and/or chemically affixed.
    Type: Grant
    Filed: April 5, 1996
    Date of Patent: July 14, 1998
    Assignee: Veba Oel AG
    Inventors: Ulrich Hoffmann, Ulrich Kunz, Hartmut Bruderreck, Klaus Gottlieb, Kuno Schadlich, Stefan Becker
  • Patent number: 5763685
    Abstract: 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: Grant
    Filed: August 17, 1995
    Date of Patent: June 9, 1998
    Assignee: Huntsman Specialty Chemicals Corporation
    Inventors: Charles Joseph Kruse, Kyle Lee Preston, Brian Lawrence Benac
  • Patent number: 5750800
    Abstract: An integrated process to produce diisopropyl ether from propane has been developed. In a first reaction zone the propane in a feedstock, after any hydrocarbons containing four or more carbon atoms are removed from the feedstock via fractionation, is dehydrogenated in the presence of a dehydrogenation catalyst to form propylene. After removing hydrogen, the propane and propylene mixture generated in the first reaction zone is separated into a propane enriched stream and a propylene enriched stream where the propylene enriched stream contains at least 65 mass % propylene. The propane enriched stream is recycled to the feedstock fractionation unit, and the propylene of the propylene enriched stream is reacted with water in a second reaction zone in the presence of an acidic catalyst to form isopropyl alcohol which is concurrently reacted with propylene to produce diisopropyl ether.
    Type: Grant
    Filed: November 9, 1995
    Date of Patent: May 12, 1998
    Assignee: UOP
    Inventors: Terry L. Marker, Brian S. Muldoon, Bryan K. Glover, Bipin V. Vora
  • Patent number: 5750798
    Abstract: A process for the production of ethers from a paraffin feedstock. The process includes a novel arrangement of dehydrogenation, isomerization, hydroisomerization, separation and etherification to provide a novel method for the production of ethers from a paraffin feedstock.
    Type: Grant
    Filed: December 13, 1995
    Date of Patent: May 12, 1998
    Assignee: Phillips Petroleum Company
    Inventors: Mark D. Scharre, Warren M. Ewert, Harold R. Hunt
  • Patent number: 5744652
    Abstract: Methyl tertiary butyl ether is prepared from TBA contaminated with oxygen-containing impurities by decomposing the impurities to gaseous products, by charging the thus-treated tertiary butyl alcohol 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: Grant
    Filed: March 10, 1997
    Date of Patent: April 28, 1998
    Assignee: Huntsman Specialty Chemicals Corp.
    Inventors: Pei-Shing Eugene Dai, Laurence Darrel Neff, Kyle Lee Preston, Rei-Yu Judy Hwan
  • Patent number: 5741953
    Abstract: 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: Grant
    Filed: August 17, 1995
    Date of Patent: April 21, 1998
    Assignee: Huntsman Specialty Chemicals Corporation
    Inventor: Kyle Lee Preston
  • Patent number: 5741951
    Abstract: 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: Grant
    Filed: December 30, 1996
    Date of Patent: April 21, 1998
    Assignee: Huntsman Specialty Chemicals Corporation
    Inventor: Kyle Lee Preston
  • Patent number: 5723687
    Abstract: A process is described for the joint production of ethers and hydrocarbons with a high octane number starting from C.sub.4 hydrocarbon cuts containing isobutene, by oligomerization with acid catalysts, in the presence of primary alcohols selected from methanol or ethanol in such a quantity as to have a molar ratio primary alcohols/isobutene in the feeding of between 0.2 and 0.7, preferably operating at a reaction temperature of between 30.degree. and 100.degree. C. and at feeding space velocities of less than 20 h.sup.-1.
    Type: Grant
    Filed: May 15, 1996
    Date of Patent: March 3, 1998
    Assignee: Snamprogetti S.p.A.
    Inventors: Mario Marchionna, Francesco Ancillotti, Marco Di Gerolamo
  • Patent number: 5723686
    Abstract: A combination process wherein a hydroisomerization system provides a hydrocarbon feed for an etherification system wherein unreacted alcohol is separated from the etherification effluent and passed to the fractionation column used in the hydroisomerization system so that water entrained in the unreacted alcohol can be separated from said alcohol within said fractionation column.
    Type: Grant
    Filed: August 3, 1995
    Date of Patent: March 3, 1998
    Assignee: Phillips Petroleum Company
    Inventors: Gary R. Patton, Robert B. Eldridge
  • Patent number: 5714640
    Abstract: A condensation reaction process and reactor for converting a plurality of reactants to at least one reaction product having a vapor pressure less than the vapor pressure of the reactants. The process includes heating a liquid phase of the reactants to at least partial vaporization thus forming a vapor phase of the reactants. The vapor phase reactants are passed in a vapor and or condensed state through at least one catalyst bed spaced from the liquid state to form reaction product(s). The reaction product(s) is returned to the liquid phase without additional contact with catalyst.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: February 3, 1998
    Assignee: Mobil Oil Corporation
    Inventors: Weldon K. Bell, Stephen H. Brown, Frederick E. Daugherty, Mohsen N. Harandi, Jeffrey C. Trewella
  • Patent number: 5705711
    Abstract: 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: Grant
    Filed: August 17, 1995
    Date of Patent: January 6, 1998
    Assignee: Huntsman Specialty Chemicals Corporation
    Inventor: Kyle Lee Preston
  • Patent number: 5705712
    Abstract: 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: Grant
    Filed: October 5, 1995
    Date of Patent: January 6, 1998
    Assignee: UOP
    Inventors: Stanley J. Frey, Robert J. Schmidt, Terry L. Marker, Richard E. Marinangeli
  • Patent number: 5689015
    Abstract: A process for the production of ethers and alkylate from a paraffin feedstock. The process includes a novel arrangement of dehydrogenation, isomerization, separation, etherification and alkylation to provide such products.
    Type: Grant
    Filed: March 8, 1996
    Date of Patent: November 18, 1997
    Assignee: Phillips Petroleum Company
    Inventors: Harold R. Hunt, Mark D. Scharre, Warren M. Ewert
  • Patent number: 5689014
    Abstract: A highly integrated process for concurrently producing diisopropyl ether and an isopropyl tertiary alkyl ether has been developed. 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 and isobutylene, isoamylene or a mixture thereof are reacted to form an isopropyl tertiary alkyl ether in a second reactor. The water present in the alcohol rich stream also reacts with the iso-olefin to form tertiary alcohol. The effluent from the second reactor is water washed to produce an oxygenate product stream and an aqueous alcohol recycle stream. Some tertiary alcohol is recycled to the first reactor where it is reacted with propylene to form additional isopropyl tertiary alkyl ether.
    Type: Grant
    Filed: October 5, 1995
    Date of Patent: November 18, 1997
    Assignee: UOP
    Inventors: Stanley J. Frey, Robert J. Schmidt, Terry L. Marker, Richard E. Marinangeli
  • Patent number: 5689013
    Abstract: The present invention concerns a process for preparing tertiary alkyl ethers. The process comprises the steps of contacting in the presence of a catalyst a feedstock containing saturated hydrocarbons and dienes having 4 to 7 carbon atoms with an excess of hydrogen in relation to the amount of dienes in the feed in order selectively to hydrogenate at least a part of the dienes, feeding the treated hydrocarbon feedstock together with at least a part of the unreacted hydrogen to a catalytic distillation reactor system which includes at least one distillation column, reacting the C.sub.4-7 isoolefines of the feedstock with methanol or ethanol in the presence of a catalyst to form tertiary alkyl ethers, subjecting the reaction mixture to distillation in the distillation column, recovering the alkyl ethers and substantially all of the unreacted hydrocarbons with the bottoms product of the distillation, withdrawing an overhead product of the distillation, which mainly contains an azeotrope of saturated C.sub.
    Type: Grant
    Filed: September 12, 1995
    Date of Patent: November 18, 1997
    Assignee: Neste Ot
    Inventors: Harri Jarvelin, Petri Lindqvist, Juha Jakkula