Preparing Esters From Hydrocarbons Patents (Class 560/241)
  • Patent number: 10745340
    Abstract: The invention provides processes and materials for the efficient and cost-effective functionalization of alkanes, such as methane from natural gas, to provide esters, alcohols, and other compounds. The method can be used to produce liquid fuels such as methanol from a natural gas methane-containing feedstock. The soft oxidizing electrophile, a compound of a main group, post-transitional element such as Tl, Pb, Bi, and I, that reacts to activate the alkane C—H bond can be regenerated using inexpensive regenerants such as hydrogen peroxide, oxygen, halogens, nitric acid, etc. Main group compounds useful for carrying out this reaction includes haloacetate salts of metals having a pair of available oxidation states, such as Tl, Pb, Bi, and I.
    Type: Grant
    Filed: February 25, 2014
    Date of Patent: August 18, 2020
    Assignee: The Scripps Research Institute
    Inventors: Roy A Periana, Brian G Hashiguchi, Michael M Konnick, Steven M Bischof
  • Publication number: 20140066649
    Abstract: The present invention relates to a process for forming vinyl acetate. The process comprises the step of providing a reaction mixture having an initial heat capacity. The reaction mixture comprises acetic acid, oxygen, ethylene, and optionally water. The process further comprises the step of adding to the reaction mixture at least one heat capacity modifier to form an increased heat capacity reaction mixture. The process further comprises the step of contacting the acetic acid, oxygen, and ethylene over a catalyst under conditions effective to form a crude vinyl acetate product. The crude vinyl acetate product comprises vinyl acetate and water.
    Type: Application
    Filed: August 26, 2013
    Publication date: March 6, 2014
    Applicant: Celanese International Corporation
    Inventors: Pieter Vismans, Naveed Aslam, Tony Hammock, Kevin Hanks, Illias S. Kotsianis, Tianshu Pan, Daniel Rangel-Osalde, Kelly Wallace
  • Patent number: 8614349
    Abstract: The present invention provides a method for oxidizing a hydrocarbon, an alcohol or an aldehyde, which comprises: oxidizing a hydrocarbon, an alcohol or an aldehyde to an alcohol, an aldehyde, a carboxylic acid or a carboxylate ester corresponding thereto, in a liquid phase having: a region in which oxygen is substantially present; and a region in which oxygen is substantially absent, in the presence of a catalyst containing a palladium, wherein the region in which oxygen is substantially absent is 0.1 to 10% by volume with respect to a total of the region in which oxygen is substantially present and the region in which oxygen is substantially absent.
    Type: Grant
    Filed: November 17, 2005
    Date of Patent: December 24, 2013
    Assignee: Asahi Kasei Chemicals Corporation
    Inventors: Koshiro Yokota, Tatsuo Yamaguchi, Toru Watanabe
  • Publication number: 20130261330
    Abstract: The present invention, in one embodiment, is to a process for inhibiting impurity formation a vinyl acetate formation reaction. The process comprises the step of providing a reactor comprising an inlet section, an outlet section, a filler (or fillers), and a catalyst block section. The filler is disposed in the outlet section. The catalyst block section may be in communication with and configured between the inlet and outlet sections. The process further comprises the steps of introducing the reactants to the inlet section and contacting the reactants in the catalyst block section under conditions effective to form a crude vinyl acetate composition. The process may further comprise the step of directing the crude vinyl acetate composition into the outlet section, which comprises the filler.
    Type: Application
    Filed: February 20, 2013
    Publication date: October 3, 2013
    Inventors: Naveed Aslam, Jessica Freeman, Ilias S. Kotsianis, Lauren Moore, Quiang Yao
  • Patent number: 8536369
    Abstract: Process for producing methyl acetate by carbonylating a dimethyl ether feed with carbon monoxide under substantially anhydrous conditions in the presence of a mordenite catalyst which has been ion-exchanged or otherwise loaded with at least one of silver and copper. The mordenite is also ion-exchanged or otherwise loaded with platinum in an amount in the range 0.05 to 10 mol % relative to aluminum.
    Type: Grant
    Filed: April 23, 2008
    Date of Patent: September 17, 2013
    Assignee: BP Chemicals Limited
    Inventors: Evert Jan Ditzel, Andre Harmen Sijpkes, John Glenn Sunley
  • Patent number: 8373003
    Abstract: The present invention relates to a method of removing heavy hydrocarbon from reaction products in producing sec-butyl acetate, characterized in that the method comprises: drawing out materials from the enrichment area of the heavy hydrocarbon; contacting the materials with water sufficiently to make the heavy hydrocarbon in materials and the water stratify naturally wherein the heavy hydrocarbon is contained in the upper layer and the water is contained in the lower layer; and discharging the upper layer and recycling the lower layer into the system.
    Type: Grant
    Filed: June 25, 2008
    Date of Patent: February 12, 2013
    Assignee: Hunan Zhongchuang Chemical Co., Ltd.
    Inventors: Xiannian Hu, Hua Li, Pingxiang Xi
  • Patent number: 8309757
    Abstract: This invention provides an integrated two stage economical process for the production of vinyl acetate monomer (VAM) from acetic acid in the vapor phase. First, acetic acid is selectively hydrogenated over a hydrogenating catalyst composition to form ethylene either in a single reactor zone or in a dual rector zone wherein the intermediate hydrogenated products are either dehydrated and/or cracked to form ethylene. In a subsequent second stage so formed ethylene is reacted with molecular oxygen and acetic acid over a suitable catalyst to form VAM. In an embodiment of this invention reaction of acetic acid and hydrogen over a hydrogenation catalyst and subsequent reaction over a dehydration catalyst selectively produces ethylene, which is further mixed with acetic acid and molecular oxygen and reacted over a supported palladium/gold/potassium catalyst.
    Type: Grant
    Filed: December 2, 2011
    Date of Patent: November 13, 2012
    Assignee: Celanese International Corporation
    Inventors: Victor Johnston, Barabra Kimmich, Deborah Repman, James Zink, Josefina Chapman, Laiyuan Chen
  • Patent number: 8207279
    Abstract: Disclosed is a method for producing a norbornene monomer composition, a norbornene polymer produced using the norbornene monomer composition, an optical film including the norbornene polymer, and a method for producing the norbornene polymer. The method includes reacting a reaction solution that contains cyclopentadiene, dicyclopentadiene, or a mixture of cyclopentadiene and dicyclopentadiene, an acetate compound, and a solvent so that a content of an exo isomer is 50 mol % or more. Variables such as a reaction temperature, a reaction time, a molar ratio between reactants, and addition of a solvent are controlled so that the exo isomer is contained in content of 50 mol % or more. Accordingly, it is possible to industrially produce an acetate norbornene addition polymer by using the acetate norbornene monomer composition containing the exo isomer in content of 50 mol % or more.
    Type: Grant
    Filed: June 26, 2007
    Date of Patent: June 26, 2012
    Assignee: LG Chem, Ltd.
    Inventors: Dai-Seung Choi, Hye-Young Jung, Sung-Don Hong, Jung-Min Lee, Hee-Jean Lee, Sung-Ho Chun
  • Publication number: 20120108842
    Abstract: In one embodiment, the invention is to a method for producing a vinyl acetate composition. The method comprises the step of contacting acetic acid, oxygen, and ethylene under conditions effective to form a crude vinyl acetate composition comprising vinyl acetate, acetic acid, residual oxygen, and water. The method further comprises the step of contacting the crude vinyl acetate composition or a derivative thereof with at least one scavenger to form a treated crude vinyl acetate composition.
    Type: Application
    Filed: October 25, 2011
    Publication date: May 3, 2012
    Applicant: Celanese International Corporation
    Inventors: Jessica Freeman, Qiang Yao, Lauren Moore, Ilias Kotsianis, Victor Johnston, Kevin Hanks
  • Patent number: 8168562
    Abstract: A new method for preparing supported palladium-gold catalysts is disclosed. The method comprises sulfating a titanium dioxide support, calcining the sulfated support, impregnating the calcined support with a palladium salt, a gold salt, and an alkali metal or ammonium compound, calcining the impregnated support, and reducing the calcined support. The resultant supported palladium-gold catalysts have increased activity and stability in the acetoxylation.
    Type: Grant
    Filed: February 2, 2006
    Date of Patent: May 1, 2012
    Assignee: Lyondell Chemical Technology, L.P.
    Inventor: Steven M. Augustine
  • Patent number: 8029748
    Abstract: The invention provides methods, apparatus and chemical systems for making vinyl acetate from ethylene, oxygen, and acetic acid.
    Type: Grant
    Filed: November 18, 2008
    Date of Patent: October 4, 2011
    Assignees: Velocys, Inc, Celanese International Corporation
    Inventors: Terry Mazanec, Victor J. Johnston, Michael Huckman, Sean P. Fitzgerald, James A. Foster, Daniel Lindley, Anna Lee Tonkovich, Francis P. Daly, Leslie Wade, Tony Hammock, Thomas Yuschak, Bin Yang, Kai Jarosch
  • Patent number: 7855303
    Abstract: This invention provides an integrated two stage economical process for the production of vinyl acetate monomer (VAM) from acetic acid in the vapor phase. First, acetic acid is selectively hydrogenated over a hydrogenating catalyst composition to form ethylene either in a single reactor zone or in a dual rector zone wherein the intermediate hydrogenated products are either dehydrated and/or cracked to form ethylene. In a subsequent second stage so formed ethylene is reacted with molecular oxygen and acetic acid over a suitable catalyst to form VAM. In an embodiment of this invention reaction of acetic acid and hydrogen over a hydrogenation catalyst and subsequent reaction over a dehydration catalyst selectively produces ethylene, which is further mixed with acetic acid and molecular oxygen and reacted over a supported palladium/gold/potassium catalyst.
    Type: Grant
    Filed: November 14, 2008
    Date of Patent: December 21, 2010
    Assignee: Celanese International Corporation
    Inventors: Victor J. Johnston, Laiyuan Chen, James H. Zink, Josefina T. Chapman, Barbara F. Kimmich, Deborah R. Repman
  • Patent number: 7718811
    Abstract: A process for reacting in a fluid bed reactor at least one oxidisable reactant with molecular oxygen in the presence of a catalytically active fluidised bed of solid particles. In the process a molecular oxygen-containing gas having an oxygen concentration greater than that of air is introduced into the fluidised bed whilst the fluidised bed is maintained in a turbulent regime. The process is suitable for oxidation, ammoxidation and carboxylation processes, including the production of maleic anhydride, acrylonitrile, ethylene, acetic acid and vinyl acetate.
    Type: Grant
    Filed: June 3, 2008
    Date of Patent: May 18, 2010
    Assignee: Ineos Europe Limited
    Inventors: Michele Fiorentino, David Newton, George Fredrick Salem, Bruce Leo Williams
  • Patent number: 7700801
    Abstract: A method of co-producing vinyl acetate and ethyl acetate includes: (a) reacting ethylene, acetic acid and oxygen to form vinyl acetate and at least a minor amount of ethyl acetate; (b) providing a crude product stream containing the vinyl acetate and ethyl acetate of step (a) and acetic acid to a distillation tower; (c) separating the crude product stream into: (i) a vinyl acetate product stream enriched in vinyl acetate with respect to the crude product stream; (ii) an acid recycle stream enriched in acetic acid with respect to the crude product stream; (iii) a mixed sidestream containing vinyl acetate and ethyl acetate, the mixed sidestream being enriched in ethyl acetate with respect to the vinyl acetate product stream; and (d) hydrogenating vinyl acetate in the mixed sidestream to provide an ethyl acetate product stream.
    Type: Grant
    Filed: November 15, 2004
    Date of Patent: April 20, 2010
    Assignee: Celanese International Corporation
    Inventors: R. Jay Warner, J. Alfonso Torres
  • Patent number: 7534910
    Abstract: The present invention provides a process for the production of an alkenyl carboxylate by reacting an alkene, a carboxylic acid and a molecular oxygen-containing gas in a reaction zone in the presence of a catalyst at an elevated reaction temperature, T, to produce an outlet stream from the reaction zone comprising alkenyl carboxylate and oxygen, and wherein in said process the catalyst is contacted with the alkene, at a partial pressure, P, optionally in the presence of the carboxylic acid, and the outlet stream comprises less than 2 vol % oxygen, the improvement comprises reducing the partial pressure of the alkene and/or reducing the reaction temperature so as to suppress formation of benzene and/or suppress inhibition of the catalyst.
    Type: Grant
    Filed: September 29, 2003
    Date of Patent: May 19, 2009
    Assignee: BP Chemicals Limited
    Inventors: Evert Jan Ditzel, Simon Frederick Thomas Froom
  • Patent number: 7518014
    Abstract: The present invention relates to a method of producing a catalyst or pre-catalyst suitable for assisting in the production of alkenyl alkanoates. The method includes contacting a modifier precursor to a support material to form a modified support material. One or more catalytic component precursors (palladium or gold) may be contacted to the modified support material. The atomic ratio of gold to palladium is preferably in the range of about 0.3 to about 0.90. The support materials with the catalytic component may then be reduced using a reducing environment. A composition for catalyzing the production of an alkenyl alkanoates including a modified support material with palladium and gold is also included within the invention. Catalysts of the present invention may be used to produce alkenyl alkanoates in general and vinyl acetate in particular and are useful to produce low EA/VA ratios while maintaining or improving CO2 selectivity.
    Type: Grant
    Filed: November 21, 2005
    Date of Patent: April 14, 2009
    Assignee: Celanese International Corp.
    Inventors: Barbara Kimmich, Leslie E. Wade, Tao Wang, André Harmen Sijpkes, Roelandus Hendrikus Wilhelmus Moonen
  • Patent number: 7491843
    Abstract: Acetic acid and/or vinyl acetate are produced by an integrated process which comprises the steps: (a) contacting in a first reaction zone a gaseous feedstock comprising ethylene and/or ethane and optionally steam with a molecular oxygen-containing gas in the presence of a catalyst active for the oxidation of ethylene to acetic acid and/or ethane to acetic acid and ethylene to produce a first product stream comprising acetic acid, water and ethylene (either as unreacted ethylene and/or as co-produced ethylene) and optionally also ethane, carbon monoxide, carbon dioxide and/or nitrogen; (b) contacting in a second reaction zone in the presence or absence of additional ethylene and/or acetic acid at least a portion of the first gaseous product stream comprising at least acetic acid and ethylene and optionally also one or more of water, ethane, carbon monoxide, carbon dioxide and/or nitrogen with a molecular oxygen-containing gas in the presence of a catalyst active for the production of vinyl acetate to produce
    Type: Grant
    Filed: November 2, 2001
    Date of Patent: February 17, 2009
    Assignee: BP Chemicals Limited
    Inventors: Simon Jobson, Derrick John Watson
  • Patent number: 7468455
    Abstract: The invention provides methods, apparatus and chemical systems for making vinyl acetate from ethylene, oxygen, and acetic acid.
    Type: Grant
    Filed: October 20, 2005
    Date of Patent: December 23, 2008
    Assignees: Velocys, Inc., Celanese International Corporation
    Inventors: Terry Mazanec, Victor J. Johnston, Michael Huckman, Sean P. Fitzgerald, James A. Foster, Daniel Lindley, Anna Lee Tonkovich, Francis P. Daly, Leslie Wade, Tony Hammock, Thomas Yuschak, Bin Yang, Kai Jarosch
  • Patent number: 7411107
    Abstract: A process for the oxidation of a C2 to C4 alkane to produce the corresponding alkene and carboxylic acid which process comprises separation of the alkene from a mixture of the alkene, the alkane and oxygen by absorption in a metallic salt solution, and recovery of an alkene-rich stream from the metallic salt solution. Integrated processes for the production of alkyl carboxylate and alkenyl carboxylate, which processes comprise oxidation of a C2 to C4 alkane to produce the corresponding alkene and carboxylic acid, separation of the alkene from a mixture of the alkene, the alkane and oxygen by absorption in a metallic salt solution, and recovery of an alkene-rich stream from the metallic salt solution for use in production of alkyl carboxylate or alkenyl carboxylate.
    Type: Grant
    Filed: February 12, 2003
    Date of Patent: August 12, 2008
    Assignee: BP Chemicals Limited
    Inventor: Andrew Richard Lucy
  • Publication number: 20080132723
    Abstract: The present invention provides an integrated, optimized process for the production of ethylene, carbon monoxide and acetic acid from an ethane feed, including reacting ethane with oxygen in the presence of a catalyst to produce ethylene, carbon monoxide and acetic acid in a reactor, wherein the catalyst comprises the elements Mo, Pd, X, and Y in the gram-atomic ratios MOa Pdb Xc Yd, and the oxygen partial pressure in the reactor is about 15 psia to about 50 psia. The partial pressure of ethane in the reactor is about 50 psia to about 150 psia.
    Type: Application
    Filed: December 4, 2006
    Publication date: June 5, 2008
    Inventors: Victor J. Johnston, Joseph G. Duff, Debra Ann Ryan, Deborah R. Repman, Melchior A. Meilchen, David W. Townsend, Cathy L. Tway
  • Patent number: 7262322
    Abstract: An oxidation process for the production of alkenes and carboxylic acids from a feed comprising alkene and/or alkane, carbon monoxide, a molecular oxygen containing gas and optionally water in the presence of an oxidation catalyst in which the level of carbon monoxide is maintained between 1% and 20% by volume of the total feed to the reactor.
    Type: Grant
    Filed: May 13, 2004
    Date of Patent: August 28, 2007
    Assignee: BP Chemicals Limited
    Inventors: Ewen James Ferguson, Andrew Richard Lucy, Mark Stephen Roberts, Diana Rachel Taylor, Bruce Leo Williams
  • Patent number: 7189883
    Abstract: This invention relates to asymmetric hydroformylation processes in which a prochiral or chiral olefin is reacted with carbon monoxide and hydrogen in the presence of an optically active metal-ligand complex catalyst to produce an optically active aldehyde or a product derived from an optically active aldehyde.
    Type: Grant
    Filed: August 25, 2005
    Date of Patent: March 13, 2007
    Inventors: Clark Landis, Thomas P. Clark, Jerzy Klosin
  • Patent number: 6946570
    Abstract: This invention relates to a process for the production of lower aliphatic esters by reacting a lower olefin with a saturated lower aliphatic mono-carboxylic acid in the vapor phase in the presence of a heteropolyacid catalyst in a plurality of reactors set up in series such that the reactant gases exiting from a first reactor are fed as the feed gas to a second reactor and those exiting from the second reactor are fed as the feed gas to a third reactor and so on for the subsequent reactors. An aliquot of the reactant monocarboxylic acid is introduced into the feed gas to the second and subsequent reactors so as to maintain the olefin to monocarboxylic acid ratio in the feed gas to each of the second and subsequent reactors within a pre-determined range.
    Type: Grant
    Filed: February 25, 2004
    Date of Patent: September 20, 2005
    Assignee: BP Chemicals Limited
    Inventors: Stanley John Becker, Geoffrey Bryne, Simon Frederick Thomas Froom, Stephen Robert Hodge
  • Patent number: 6852877
    Abstract: A process for the production of vinyl acetate comprising contacting in a first reaction zone a gaseous feedstock comprising essentially ethane with a molecular oxygen-containing gas in the presence of a catalyst to produce a first product stream comprising acetic acid; contacting in a second reaction zone a gaseous feedstock comprising essentially ethane with a molecular oxygen-containing gas in the product stream comprising ethylene; contacting in a third reaction one the first gaseous product stream and the second gaseous product stream with a molecular oxygen-containing gas in the presence of a catalyst to produce a fourth product stream comprising vinyl acetate; separating the product stream from step (3) and recovering vinyl acetate from said product stream from step (3).
    Type: Grant
    Filed: May 19, 2000
    Date of Patent: February 8, 2005
    Assignee: Celanese International Corp.
    Inventors: Sabine Zeyss, Uwe Dingerdissen, John Fritch
  • Publication number: 20040249192
    Abstract: Process for treating a mixed C4 stream comprising iso-butene and 1,3-butadiene by (a) reacting the stream with acetic acid in an addition reactor, (b) withdrawing product comprising iso-butene, sec-butenyl acetate, n-butenyl acetate and t-butyl acetate, and recovering n-butenyl acetate from the product and separating and recycling t-butyl acetate to the addition reactor. The process provides increased efficiency of acetic acid utilisation together with useful products, e.g. n-butenyl and sec-butenyl acetates which can be separated and sold as such or converted to other products. The unreacted isobutene can be separated and used as such, or recycled and allowed to dimerise to di-isobutene, another useful product.
    Type: Application
    Filed: June 16, 2004
    Publication date: December 9, 2004
    Inventors: Benjamin Patrick Gracey, Nicholas John Hazel
  • Publication number: 20040242918
    Abstract: A catalyst for use in producing a lower aliphatic carboxylic acid ester, wherein the catalyst is produced by a process comprising a step of contacting the catalyst with a gas containing at least one member selected from water, lower aliphatic carboxylic acids and lower aliphatic alcohols; a process for producing the catalyst; and a process for producing a lower aliphatic carboxylic acid ester using the catalyst. The catalyst can exhibit high initial activity and high space time yield, ensure sufficiently long catalyst life in practice in industry, and can prevent the production of by-product materials. A siliceous support for use in a catalyst, which has a silicon content of from 39.7 to 46.3% by mass or a silicon content of from 85 to 99% by mass in terms of silicon dioxide or a crush strength of 30 N or more.
    Type: Application
    Filed: February 25, 2004
    Publication date: December 2, 2004
    Applicant: SHOWA DENKO K.K
    Inventors: Etsuko Kadowaki, Tomoyoshi Higashi, Wataru Oguchi, Hiroshi Uchida, Kousuke Narumi
  • Patent number: 6825149
    Abstract: A shell impregnated catalyst of Pd-Au produced on a silica support to have a Pd loading of 1.8 g/L of catalyst to about 7.2 g/L and a Au to Pd weight ratio of 0.3 to 2.0 by impregnating the support with aqueous solutions of palladium and gold salts or acids and thereafter precipitating water insoluble compounds of Pd and Au on the with alkali metal silicate or hydroxide solutions, then dried, and the surface precipitated compounds of Pd and Au are then reduced by reaction with ethylene or hydrogen at a temperature of greater than 150° C. up to 310° C. or with hydrogen up to 299° C. until substantially all of the Pd and Au contents are reduced to a free metal state, after which the support is impregnated with potassium acetate to an extent of 6 to 7 weight percent of the weight of the total catalyst.
    Type: Grant
    Filed: June 19, 2002
    Date of Patent: November 30, 2004
    Assignee: Saudi Basic Industries Corporation
    Inventor: Alla Konstantin Khanmamedova
  • Patent number: 6809218
    Abstract: Porous microcomposites have been prepared from perfluorinated ion-exchange polymer and metal oxides such as silica using the sol-gel process. Such microcomposites possess high surface area and exhibit extremely high catalytic activity.
    Type: Grant
    Filed: October 7, 2003
    Date of Patent: October 26, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6794535
    Abstract: Process for the production of lower aliphatic esters comprising reacting a lower olefin with a saturated lower aliphatic monocarboxylic acid in the vapor phase in the presence of a heteropolyacid catalyst. The reaction is carried out in a plurality of reactors set up in series, and the feedstock is rendered substantially free of metallic or metal compound impurities prior to being brought into contact with the heteropolyacid catalyst.
    Type: Grant
    Filed: January 3, 2001
    Date of Patent: September 21, 2004
    Assignee: BP Chemicals Limited
    Inventors: Simon Frederick Thomas Froom, Stephen Robert Hodge, Witold Franciszek Pacynko
  • Publication number: 20040181088
    Abstract: A process for producing a lower aliphatic carboxylic acid ester comprising reacting a lower aliphatic carboxylic acid and a lower olefin in the presence of a catalyst, wherein the raw materials contain substantially no halogens. The catalyst used can be remarkably prevented from deteriorating and a stable operation of the process can be continuously performed for an extended period.
    Type: Application
    Filed: April 29, 2004
    Publication date: September 16, 2004
    Inventors: Kyoichi Watanabe, Hiroshi Uchida
  • Publication number: 20040167353
    Abstract: This invention relates to a process for the production of lower aliphatic esters by reacting a lower olefin with a saturated lower aliphatic mono-carboxylic acid in the vapour phase in the presence of a heteropolyacid catalyst in a plurality of reactors set up in series such that the reactant gases exiting from a first reactor are fed as the feed gas to a second reactor and those exiting from the second reactor are fed as the feed gas to a third reactor and so on for the subsequent reactors. An aliquot of the reactant monocarboxylic acid is introduced into the feed gas to the second and subsequent reactors so as to maintain the olefin to monocarboxylic acid ratio in the feed gas to each of the second and subsequent reactors within a pre-determined range.
    Type: Application
    Filed: February 25, 2004
    Publication date: August 26, 2004
    Applicant: BP Chemicals Limited
    Inventors: Stanley John Becker, Geoffrey Bryne, Simon Frederick Thomas Froom, Stephen Robert Hodge
  • Patent number: 6781014
    Abstract: The retrofitting of an existing methanol or methanol/ammonia plant to make acetic acid is disclosed. The existing plant has a reformer (10) to which natural gas or another hydrocarbon and steam (water) are fed. Syngas is formed in the reformer (10). All or part of the syngas is process to separate out carbon dioxide (24), carbon monoxide (30) and hydrogen (32), and the separated carbon dioxide (24) is the existing to the existing methanol synthesis loop (12) for methanol synthesis, or back into the feed to the reformer (10) to enhance carbon monoxide formation in the syngas (18). Any remaining syngas (38) not fed to the carbon dioxide separator (22) can be converted to methanol in the existing methanol synthesis loop (12) along with carbon dioxide (24) from the separator (22) and/or imported carbon dioxide (25), and hydrogen (35) from the separator (28). The separated carbon monoxide (30) is then reacted with the methanol (36) to produce acetic acid (40) or an acetic acid precursor by a conventional process.
    Type: Grant
    Filed: April 30, 2002
    Date of Patent: August 24, 2004
    Assignee: Acetex (Cyprus) Limited
    Inventors: Kenneth Ebenes Vidalin, Daniel Marcel Thiebaut
  • Patent number: 6770791
    Abstract: Disclosed is an olefin containing stream from an oxygenate to olefin process, and a process for making olefin dimer and oligomer product from the olefin containing stream using a nickel based oligomerization catalyst. The dimer/oligomer product is optionally converted to hydroformylated product. The olefin containing stream that is used to make the higher olefin product has low levels of impurities including nitrogen, sulfur and/or chlorine.
    Type: Grant
    Filed: April 29, 2003
    Date of Patent: August 3, 2004
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Georges Mathys, John Stephen Godsmark, Marcel Janssen, Luc Roger Martens, Hubertus Joseph Beckers, Eddy Theophile Andrea Van Driessche, Raphael Frans Ivo Caers, John Richard Shutt
  • Publication number: 20040143132
    Abstract: A catalyst for use in the production of a lower aliphatic carboxylic acid ester by reacting a lower olefin and a lower aliphatic acid ester in a gas phase, which catalyst has been decreased in activity through use, is regenerated by heating to be recovered in activity. The regenerated catalyst is reused for the production of a lower aliphatic carboxylic acid ester.
    Type: Application
    Filed: November 18, 2003
    Publication date: July 22, 2004
    Inventors: Etsuko Kadowaki, Kyoichi Watanabe, Yumiko Obata, Hiroshi Uchida
  • Publication number: 20040106822
    Abstract: A fluid bed process for the manufacture of vinyl acetate from ethylene, acetic acid and oxygen comprising feeding ethylene and acetic acid into a fluid bed reactor through a first inlet, introducing the oxygen into the reactor through a second inlet, co-joining the oxygen, ethylene and acetic acid in the reactor in contact with a fluid bed catalyst to produce vinyl acetate. The particle size diameter of the particulate catalyst material has a range of 60% of the particles being below 200 microns (0.1 mm) with no more than 40% of the particles being below 40 microns (0.04 mm).
    Type: Application
    Filed: November 25, 2003
    Publication date: June 3, 2004
    Inventors: Larry M. Cirjak, Michael F. Lemanski, David R. Wagner, Nancy C. Benkalowycz, Patricia R. Blum, Marc A. Pepera, Christos Paparizos
  • Patent number: 6727380
    Abstract: A process for the oxidation of a C2 to C4 alkane to produce the corresponding alkene and carboxylic acid which process comprises contacting in an oxidation reaction zone, said alkane, molecular oxygen-containing gas, and optionally, at least one of the corresponding alkene and water, in the presence of at least two catalysts each active, with different selectivities, for the oxidation of the alkane to the corresponding alkene and carboxylic acid, to produce a product stream comprising said alkene, carboxylic acid and water, and in which process the molar ratio of alkene to carboxylic acid produced in said oxidation reaction zone is adjusted or maintained at a pre-determined value by controlling the relative proportions of the at least two catalysts in said oxidation reaction zone. Such an oxidation process may be used in an integrated process, such as for the manufacture of ethyl acetate or vinyl acetate.
    Type: Grant
    Filed: February 21, 2003
    Date of Patent: April 27, 2004
    Assignee: BP Chemicals Limited
    Inventors: Brian Ellis, Mark Stephen Roberts
  • Publication number: 20030233011
    Abstract: This invention relates to a process for producing a mixture of levulinic acid esters and formic acid esters from biomass and olefins, and the composition prepared therefrom. This invention also relates to usage of the mixture of these esters as fuel and as fuel additives for gasoline fuel, diesel fuel, and biofuel.
    Type: Application
    Filed: April 1, 2003
    Publication date: December 18, 2003
    Inventors: Paul Joseph Fagan, Ekaterini Korovessi, Leo Ernest Manzer, Rakesh H. Mehta, Stuart M. Thomas
  • Publication number: 20030191340
    Abstract: Complexes of a selected class of chiral ligands with molybdenum, tungsten or chromium, preferably molybdenum, are effective as catalysts in highly enantioselective and regioselective alkylation of allylic substrates.
    Type: Application
    Filed: February 5, 2003
    Publication date: October 9, 2003
    Inventors: Barry M. Trost, Iwao Hachiya
  • Publication number: 20030187294
    Abstract: The invention relates to a method for producing a catalyst containing one or several metals from the group of metals comprising the subgroups Ib and VIIIb of the periodic table on porous support particles, characterised by a first step in which one or several precursors from the group of compounds of metals from sub-groups Ib and VIIIb of the periodic table is or are applied to a porous support, and a second step in which the porous, preferably nanoporous support to which at least one precursor has been applied is treated with at least one reduction agent, to obtain the metal nanoparticles produced in situ in the pores of said support.
    Type: Application
    Filed: March 24, 2003
    Publication date: October 2, 2003
    Applicant: Celanese Chemical Europe GmbH
    Inventors: Alfred Hagemeyer, Uwe Dingerdissen, Klaus Kuhlein, Andreas Manz, Roland Fischer
  • Publication number: 20030187293
    Abstract: A process for preparing a catalyst which process comprises the steps of:
    Type: Application
    Filed: March 24, 2003
    Publication date: October 2, 2003
    Inventors: Peter Birke, Hans-Dieter Neubauer, Rainer Schubert
  • Publication number: 20030181754
    Abstract: The tert-butyl ester of an aliphatic C1-C4-carboxylic acid is prepared by reacting the carboxylic acid with isobutene in the liquid phase in the presence of an acidic catalyst by a continuous process in which the reaction is carried out in a reactor divided into a plurality of sections, the carboxylic acid, the isoolefin and the catalyst are fed into the first section of the reactor, the reaction mixture obtained is removed from the last section of the reactor and the ester is isolated therefrom, the reaction temperature in the reactor being controlled so that it is from 10 to 40° C. and is highest in the first section of the reactor.
    Type: Application
    Filed: January 27, 2003
    Publication date: September 25, 2003
    Inventors: Ruprecht Kroker, Gerhard Nestler, Werner Schmitt, Winfried Schumm
  • Publication number: 20030176729
    Abstract: Porous microcomposites have been prepared from perfluorinated ion-exchange polymer and metal oxides such as silica using the sol-gel process. Such microcomposites possess high surface area and exhibit extremely high catalytic activity.
    Type: Application
    Filed: December 18, 2002
    Publication date: September 18, 2003
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6548697
    Abstract: A process for the oxidation of a C2 to C4 alkane to produce the corresponding alkene and carboxylic acid which process comprises contacting in an oxidation reaction zone, said alkane, molecular oxygen-containing gas, and optionally, at least one of the corresponding alkene and water, in the presence of at least two catalysts each active, with different selectivities, for the oxidation of the alkane to the corresponding alkene and carboxylic acid, to produce a product stream comprising said alkene, carboxylic acid and water, and in which process the molar ratio of alkene to carboxylic acid produced in said oxidation reaction zone is adjusted or maintained at a pre-determined value by controlling the relative proportions of the at least two catalysts in said oxidation reaction zone. Such an oxidation process may be used in an integrated process, such as for the manufacture of ethyl acetate or vinyl acetate.
    Type: Grant
    Filed: July 18, 2002
    Date of Patent: April 15, 2003
    Assignee: BP Chemicals Limited
    Inventors: Brian Ellis, Mark Stephen Roberts
  • Patent number: 6534672
    Abstract: A catalytically active material useful to prepare vinyl acetate monomer from ethylene, acetic acid, and an oxygen-containing gas under fluid bed conditions comprises a porous microspheroidal support containing catalytically active palladium crystallites finely dispersed within the support. This catalyst material does not require incorporation of gold to maintain activity and selectivity. A process to produce a vinyl acetate fluid bed catalyst in which catalytically active small palladium crystallites are finely dispersed within the support comprises dispersing selected metal species within the support which have an affinity to palladium to form very fine crystallites of palladium. The affinity metal species may be dispersed by impregnation onto a preformed microspheroidal support or may be intimately incorporated within the support before impregnation with a soluble palladium species.
    Type: Grant
    Filed: December 4, 2001
    Date of Patent: March 18, 2003
    Assignee: The Standard Oil Company
    Inventors: George Frederick Salem, Michael James Baker
  • Publication number: 20030040641
    Abstract: A process for producing a lower aliphatic carboxylic acid ester by a gas phase esterification reaction starting from a lower aliphatic carboxylic acid and a lower olefin, comprising adding a lower alcohol corresponding to a hydrate of a lower olefin to the gas phase reaction product, condensing a lower aliphatic carboxylic acid and the lower alcohol and while allowing the conversion into a lower aliphatic carboxylic acid ester to proceed, separating the lower aliphatic carboxylic acid ester. Productivity is increased due to the improvement of the conversion of a lower aliphatic carboxylic acid.
    Type: Application
    Filed: December 14, 2001
    Publication date: February 27, 2003
    Inventors: Ayumu Fujita, Etsuko Kadowaki, Meiko Saihata, Hiroshi Uchida
  • Patent number: 6472556
    Abstract: A catalyst for use in the production of vinyl acetate which comprises (1) a catalyst support, (2) palladium, (3) an acid, (4) at least one acetic acid catalyst promoter and (5) at least one vinyl acetate promoter and/or co-promoter. A process for the production of vinyl acetate from ethylene and an oxygen-containing gas using the catalyst.
    Type: Grant
    Filed: March 27, 2001
    Date of Patent: October 29, 2002
    Assignee: BP Chemicals Limited
    Inventors: Simon James Kitchen, Daiyi Qin
  • Patent number: 6465683
    Abstract: Process for making a butyl ester from butadiene, comprising (a) reacting butadiene with a saturated aliphatic monocarboxylic acid to form a mixture of n-butenyl and secondary butenyl esters, (b) separating the n-butenyl ester from the secondary butenyl ester, and (c) hydrogenating the n-butenyl ester separated in step (b) in the presence of a catalyst to the corresponding n-butyl ester.
    Type: Grant
    Filed: April 30, 2001
    Date of Patent: October 15, 2002
    Assignee: BP Chemicals Limited
    Inventors: Benjamin Patrick Gracey, Norbert Walter Josef Kamp
  • Patent number: 6455023
    Abstract: Carbon monolith-supported catalysts with high leach resistance used in catalytic applications involving strong acidic and basic conditions in a pH range of from 0 to 6.5 and from 7.5 to 14, are respectively described. The leach resistance of the catalyst system originates from strong interaction between the catalyst and the unsaturated valence of the carbon surface. In addition to surprisingly high resistance to leach out, the catalysts also have substantial differential advantages in catalyst performance: catalyst activity, selectivity, and stability.
    Type: Grant
    Filed: October 11, 2000
    Date of Patent: September 24, 2002
    Assignee: Corning Incorporated
    Inventors: Kishor P. Gadkaree, Tinghong Tao
  • Patent number: RE38864
    Abstract: Process for making a butyl ester from butadiene, comprising (a) reacting butadiene with a saturated aliphatic monocarboxylic acid to form a mixture of n-butenyl and secondary butenyl esters, (b) separating the n-butenyl ester from the secondary butenyl ester, and (c) hydrogenating the n-butenyl ester separated in step (b) in the presence of a catalyst to the corresponding n-butyl ester.
    Type: Grant
    Filed: September 29, 2004
    Date of Patent: November 1, 2005
    Assignee: The University of Southern Mississippi Research Foundation
    Inventors: Benjamin Patrick Gracey, Norbert Walter Josef Kamp
  • Patent number: RE44206
    Abstract: An oxidation process for the production of alkenes and carboxylic acids from a feed comprising alkene and/or alkane, carbon monoxide, a molecular oxygen containing gas and optionally water in the presence of an oxidation catalyst in which the level of carbon monoxide is maintained between 1% and 20% by volume of the total feed to the reactor.
    Type: Grant
    Filed: May 16, 2011
    Date of Patent: May 7, 2013
    Assignee: BP Chemicals Limited
    Inventors: Ewen James Ferguson, Andrew Richard Lucy, Mark Stephen Roberts, Diana Rachel Taylor, Bruce Leo Williams