Carbon Monoxide Or Peroxy Containing Reactant Patents (Class 568/342)
  • Patent number: 10882034
    Abstract: Catalysts for the dehydration of lactic acid, lactic acid derivatives, or mixtures thereof to acrylic acid, acrylic acid derivatives, or mixtures thereof in liquid phase comprising an ionic liquid (IL) and an acid are provided.
    Type: Grant
    Filed: April 16, 2019
    Date of Patent: January 5, 2021
    Assignee: The Procter & Gamble Company
    Inventors: Jakob Albert, Peter Wasserscheid, Nicola Taccardi, Jens Nagengast, Matthias Kehrer, Julian Kadar, Dimitris Ioannis Collias
  • Patent number: 10364151
    Abstract: A catalyst for decomposing high-concentration hydrogen peroxide comprises an active layer on a carrier comprising gamma-phase alumina. The carrier can also comprise aluminum, with the gamma-phase alumina forming a passivating layer on the surface of the aluminum. The active layer can comprise platinum. Apparatus for decomposing hydrogen peroxide can include the catalyst in a decomposition chamber arranged to receive hydrogen peroxide. The apparatus can be used as a thruster, comprising a nozzle arranged to generate thrust by directing exhaust gases in a specific direction. For example, the thruster can be a monopropellant, bipropellant, or hybrid thruster. In other embodiments, the apparatus can be used as a gas generator or a fuel cell.
    Type: Grant
    Filed: September 8, 2014
    Date of Patent: July 30, 2019
    Assignee: Airbus Defence and Space Limited
    Inventors: Jonathan Thomas William Wynn, Anthony Joseph Musker
  • Patent number: 10307745
    Abstract: Catalysts for the dehydration of lactic acid, lactic acid derivatives, or mixtures thereof to acrylic acid, acrylic acid derivatives, or mixtures thereof in liquid phase comprising an ionic liquid (IL) and an acid are provided.
    Type: Grant
    Filed: July 27, 2017
    Date of Patent: June 4, 2019
    Assignee: The Procter & Gamble Company
    Inventors: Jakob Albert, Peter Wasserscheid, Nicola Taccardi, Jens Nagengast, Matthias Kehrer, Julian Kadar, Dimitris Ioannis Collias
  • Patent number: 10099985
    Abstract: This invention provides producing having an objective ketone and/or alcohol by decomposing of a hydrocarbon compound rapidly and selectively having a same number of carbon atoms as a hydrocarbon compound by decomposing a hydroperoxide in a reaction solution obtained from oxidizing the hydrocarbon compound using molecular oxygen of this invention involves, a hydroperoxide decomposition step for decomposing the hydroperoxide into the ketone and/or alcohol by contacting the reaction solution with an aqueous solution containing a carbonate of an alkaline earth metal or a carbonate of an alkali metal and a transition metal compound, a separation step for separating into an oil phase comprising the ketone and/or alcohol, and a water phase comprising the carbonate of an alkaline earth metal or carbonate of an alkali metal and the transition metal compound, a recovery step for recovering the carbonate of an alkali metal or carbonate of an alkaline earth metal and the transition metal compound by combusting the water
    Type: Grant
    Filed: October 5, 2015
    Date of Patent: October 16, 2018
    Assignee: UBE INDUSTRIES, LTD.
    Inventors: Kazunori Kurosawa, Yoshinori Sugimura, Hideo Shimomura, Kazuo Yamato, Joji Funatsu, Naoya Katagiri, Junichi Kugimoto, Joji Kawai
  • Patent number: 9975116
    Abstract: Process for the manufacture of at least one alcohol and/or at least one ketone, which comprises a step during which at least one organic peroxide compound is put into contact with at least one catalyst responding to formula (I) CrNxOy Formula (I) in which x is a number varying from 0.10 to 1.00 and y is a number varying from 0.00 to 1.50, in order to produce the at least one alcohol and/or at least one ketone.
    Type: Grant
    Filed: November 20, 2015
    Date of Patent: May 22, 2018
    Assignee: Rhodia Operations
    Inventors: Sandra Chouzier, Luis Fernando Rascon Cruz, Bert Weckhuysen, Sergio Mastroianni
  • Patent number: 9718744
    Abstract: Disclosed is a hydroalkylation process in which the hydroalkylation catalyst is activated in the presence of a flowing fluid comprising hydrogen and a condensable agent. The presence of the condensable agent enables fast, effective activation of the hydroalkylation catalyst precursor in a cost-effective manner. It also yields superior catalyst performance.
    Type: Grant
    Filed: September 26, 2014
    Date of Patent: August 1, 2017
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Gabor Kiss, Thomas E. Green, Keith H. Kuechler
  • Patent number: 9663430
    Abstract: A process for making phenol and/or cyclohexanone, the process comprising: (A) oxidizing a cyclohexylbenzene feed to obtain an oxidation product comprising cyclohexylbenzene, cyclohexylbenzene hydroperoxide and water; (B) removing at least a portion of the water from at least a portion of the oxidation product to obtain a cleavage feed; and (C) contacting at least a portion of the cyclohexylbenzene hydroperoxide in the cleavage feed with an acid catalyst in a cleavage reactor under cleavage conditions to obtain a cleavage product comprising phenol and cyclohexanone. The removing step may also comprises a step of removing a portion of the cyclohexylbenzene contained in the oxidation product. Water removal may be advantageously conducted in a water flashing drum before a cyclohexylbenzene hydroperoxide concentrator.
    Type: Grant
    Filed: August 27, 2014
    Date of Patent: May 30, 2017
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Francisco M. Benitez, Christopher L. Becker, Keith H. Kuechler, Jason D. Davis
  • Patent number: 9656934
    Abstract: In a process for producing phenol, a cleavage feed comprising cyclohexylbenzene hydroperoxide is supplied to a cleavage reaction zone and a cleavage reaction mixture comprising the cleavage feed is contacted in the cleavage reaction zone with a solid acid catalyst under conditions effective to produce a cleavage effluent comprising phenol and cyclohexanone. The cleavage effluent is then divided into at least a cleavage product and a cleavage recycle and the cleavage recycle and a polar solvent is supplied to the cleavage reaction zone to produce the cleavage reaction mixture with the cleavage feed. Preferably, the polar solvent is combined with the cleavage recycle before being charged into the cleavage reaction zone.
    Type: Grant
    Filed: June 6, 2014
    Date of Patent: May 23, 2017
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Hari Nair, Christopher L. Becker, Karen S. Nimmo, James R. Lattner, Francisco M. Benitez, Charles Morris Smith
  • Patent number: 9650324
    Abstract: A novel method for synthesis of khusimone, by bringing zizanal into contact with an oxidizing reagent in the presence of a base and an organic solvent.
    Type: Grant
    Filed: June 25, 2014
    Date of Patent: May 16, 2017
    Assignees: ROBERTET SA, UNIVERSITE DE NICE SOPHIA ANTIPOLIS, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)
    Inventors: Emilie Belhassen, Nicolas Baldovini, Jean-Jacques Filippi, Hugues Brevard
  • Patent number: 9546121
    Abstract: A process for making phenol and/or cyclohexanone comprises: (A) oxidizing a cyclohexylbenzene feed to obtain an oxidation product comprising cyclohexylbenzene, cyclohexyl-1-phenyl-1-hydroperoxide and phenol; (B) separating at least a portion of the oxidation product to obtain a first fraction comprising cyclohexyl-1-phenyl-1-hydroperoxide and a second fraction comprising cyclohexylbenzene and phenol; (C) removing at least a portion of the phenol from at least a portion of the second fraction to obtain a third fraction; (D) recycling at least a portion of the cyclohexylbenzene in the third fraction to the oxidizing step (A); and (E) contacting at least a portion of the cyclohexyl-1-phenyl-1-hydroperoxide in the first fraction with an acid catalyst in a cleavage reactor under cleavage conditions to obtain a cleavage product comprising phenol and cyclohexanone.
    Type: Grant
    Filed: October 17, 2014
    Date of Patent: January 17, 2017
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Bryan A. Patel, Jihad M. Dakka
  • Patent number: 9469589
    Abstract: In a process for producing phenol and/or cyclohexanone, cyclohexylbenzene is contacted with an oxygen-containing gas in the presence of an oxidation catalyst under oxidation conditions effective to produce an oxidation effluent comprising cyclohexylbenzene hydroperoxide. At least a portion of the oxidation effluent is then subjected to a concentrating step to produce a cleavage feed having a higher concentration of cyclohexylbenzene hydroperoxide than the oxidation effluent. A cleavage reaction mixture comprising the cleavage feed is then contacted with a solid acid catalyst in a cleavage reaction zone under conditions effective to produce a cleavage product comprising phenol and cyclohexanone.
    Type: Grant
    Filed: June 4, 2014
    Date of Patent: October 18, 2016
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Hari Nair, Christopher L. Becker, Jason D. Davis, Charles Morris Smith
  • Patent number: 9469580
    Abstract: Disclosed herein is a process for dehydrogenating a hydrocarbon with a dehydrogenation catalyst comprising a step of activating the catalyst precursor in a H2-containing atmosphere. A particularly advantageous activation process includes heating the catalyst precursor to a temperature in a range from 400° C. to 600° C. The process of the present disclosure is particularly advantageous for dehydrogenating cyclohexane to make benzene.
    Type: Grant
    Filed: November 18, 2013
    Date of Patent: October 18, 2016
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Tan-Jen Chen, Christopher L. Becker, Hari Nair, Francisco M. Benitez, Charles Morris Smith
  • Patent number: 9464047
    Abstract: Method for concentrating an organic hydroperoxide mixture comprising a hydrocarbon and a hydroperoxide corresponding thereto comprises evaporating a first liquid mixture in a thin-film evaporation device followed by separation in a separation zone. Both the evaporation device and the separation zone operate at a low absolute pressure at a temperature lower than the thermal degradation temperature of the hydroperoxide to prevent thermal decomposition thereof. The process is particularly useful for concentrating an oxidation product made from the oxidation of cyclohexylbenzene.
    Type: Grant
    Filed: June 6, 2014
    Date of Patent: October 11, 2016
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jason D. Davis, Christopher L. Becker, Travis A. Reine, Bryan A. Patel
  • Patent number: 9464020
    Abstract: In a process for separating a mixture comprising cyclohexanone and phenol, at least a portion of the mixture is distilled in the presence of a solvent including at least two alcoholic hydroxyl groups attached to non-adjacent saturated carbon atoms and at least one hemiketal defined by the formula (I) or the formula (II): wherein R1, the same or different at each occurrence, is independently an alkylene group having from 2 to 10 carbon atoms, R2 is an alkylene group having from 4 to 10 carbon atoms, and R3 is hydrogen or the following group: and/or an enol-ether derived from the hemiketal defined by the formula (I) or the formula (II), wherein the total concentration of the hemiketal and the enol-ether, expressed in terms of weight percentage on the basis of the total weight of the feed to the distilling step (a), is at least 0.01%.
    Type: Grant
    Filed: April 9, 2013
    Date of Patent: October 11, 2016
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Keith H. Kuechler, Francisco M. Benitez, Krystle J. Emanuele, Christopher L. Becker, John L. Heidman, Jr.
  • Patent number: 9452418
    Abstract: A gold/titanium nanotube-multiwalled carbon nanotube composite (Au/TNT-MWCNT) is presented. The gold composition comprises at least 3% weight of the nanotube composite based on the total weight of the nanotube composite and the gold composition is located in at least one of the wall of the titanium nanotube and the wall of the multiwalled carbon nanotube. Photocatalytic oxidation of neat cyclohexane (CHA) with H2O2 as an oxidant was carried out. Au/TNT-MWCNT catalysts promoted partial CHA oxidation with high conversion (6-7.5%) and selectivity (60-75%) to cyclohexanone.
    Type: Grant
    Filed: January 23, 2015
    Date of Patent: September 27, 2016
    Assignee: Umm Al-Qura University
    Inventors: Saleh Abdel-Mgeed Ahmed Saleh, Mohamed Mokhtar Mohamed Abdalla, Khalid Soliman Khalil Khairou
  • Patent number: 9409841
    Abstract: A process for producing phenol and/or cyclohexanone by cleaving cyclohexylbenzene hydroperoxide in a loop cleavage reactor comprising multiple reaction zones connected in series. In desirable embodiments, fresh cyclohexylbenzene hydroperoxide feed(s) are supplied to reaction zones the final reaction zone, and fresh acid catalyst is supplied only to the final reaction zone. In desirable embodiments, a portion of the effluent exiting the final reaction zone is recycled to the first reaction zone. Each reaction zone is equipped with a heat exchanger downstream of the feed port to extract heat generated from the cleavage reaction.
    Type: Grant
    Filed: March 24, 2014
    Date of Patent: August 9, 2016
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jason D. Davis, Christopher L. Becker, Bryan A. Patel, John S. Coleman, Hari Nair
  • Patent number: 9382178
    Abstract: In a process for producing phenol and cyclohexanone, reaction components comprising cyclohexylbenzene hydroperoxide and an acid catalyst are supplied to a cleavage reaction zone, mixed under mixing conditions effective to combine the reaction components into a reaction mixture and at least part of the cyclohexylbenzene hydroperoxide in the reaction mixture is converted under cleavage conditions to into phenol and cyclohexanone; and a cleavage effluent is recovered from the cleavage reaction zone. The cleavage and mixing conditions are controlled such that the ratio tR/tM is at least 10, where tR is the half-life of cyclohexylbenzene hydroperoxide under the cleavage conditions and tM is the time required after injection of a tracer material into the reaction mixture under the mixing conditions for at least 95% by volume of the entire reaction mixture to attain at least 95% of the volume-averaged tracer material concentration.
    Type: Grant
    Filed: April 9, 2014
    Date of Patent: July 5, 2016
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Bryan A. Patel, John S. Coleman
  • Patent number: 9365474
    Abstract: Disclosed herein are processes for producing phenol. The processes include oxidizing cyclohexylbenzene to produce an oxidation composition comprising cyclohexyl-1-phenyl-1-hydroperoxide. The cyclohexyl-1-phenyl-1-hydroperoxide in the oxidation composition may undergo a cleavage reaction to produce a cleavage reaction mixture comprising phenol, cyclohexanone and at least one contaminant. The cleavage reaction mixture may be contacted with a basic material to convert at least a portion of the contaminant to a converted contaminant, thereby producing a modified reaction mixture.
    Type: Grant
    Filed: August 16, 2011
    Date of Patent: June 14, 2016
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Keith Holroyd Kuechler, Francisco Manuel Benitez, Kun Wang, James R. Lattner, Christopher Lynn Becker
  • Patent number: 9321711
    Abstract: A system for producing high-purity phenol and/or cyclohexanone from cyclohexylbenzene oxidation includes a cyclohexylbenzene feed hydrogenation reactor, a bubble column oxidation reactor, a cyclohexylbenzene hydroperoxide concentrator, a cleavage reactor, and a separation and purification sub-system. The components and the integrated system are designed such that high-purity phenol and/or cyclohexanone can be produced at high energy efficiency.
    Type: Grant
    Filed: February 21, 2014
    Date of Patent: April 26, 2016
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Christopher L. Becker, James R. Lattner, Francisco M. Benitez, Charles Morris Smith
  • Patent number: 9314776
    Abstract: This invention relates to a composite oxide, production and use thereof as a methane selective oxidizing catalyst. The composite oxide has a composition as illustrated by the formula RhRxMoyVzO?-?, wherein the symbols are as defined in the specification. When used as a methane selective oxidizing catalyst, the present composite oxide provides a high methane conversion and a high selectivity to the aimed products.
    Type: Grant
    Filed: October 10, 2013
    Date of Patent: April 19, 2016
    Assignees: CHINA PETROLEUM & CHEMICAL CORPORATION, FUSHUN RESEARCH INSTITUTE OF PETROLEUM AND PETROCHEMICALS, SINOPEC
    Inventors: Shudong Zhang, Yingjie Jin, Xiangqian Ni, Jie Li, Xiwen Zhang, Xinwei Zhang
  • Patent number: 9181165
    Abstract: In a process for separating a mixture comprising cyclohexanone and phenol, at least a portion of the mixture is distilled in the presence of a solvent including at least two alcoholic hydroxyl groups attached to non-adjacent saturated carbon atoms, water, and in the presence or absence of a hemiketal defined by the formula (I) or the formula (II): wherein R1, the same or different at each occurrence, is independently an alkylene group having from 2 to 10 carbon atoms, R2 is an alkylene group having from 4 to 10 carbon atoms and/or R3 is hydrogen or the following group: and in the presence or absence of an enol-ether derived from the hemiketal defined by the formula (I) or the formula (II), wherein the total concentration of the hemiketal and enol-ether, expressed in term of weight percentage of the total weight of the feed to the distilling step, is at most 0.01%.
    Type: Grant
    Filed: April 9, 2013
    Date of Patent: November 10, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Keith H. Kuechler, Francisco M. Benitez, Krystle J. Emanuele, Christopher L. Becker, John L. Heidman, Jr.
  • Patent number: 9169181
    Abstract: In a process for producing cyclohexylbenzene hydroperoxide, cyclohexylbenzene is contacted with oxygen to produce a reaction product comprising cyclohexylbenzene hydroperoxide and unreacted cyclohexylbenzene. The reaction product is then maintained under conditions such that crystals of cyclohexylbenzene hydroperoxide form and separate from the reaction product. The cyclohexylbenzene hydroperoxide crystals are then recovered from the reaction product.
    Type: Grant
    Filed: November 28, 2011
    Date of Patent: October 27, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Kun Wang, Edmund John Mozeleski, Jihad Mohammed Dakka
  • Publication number: 20150105589
    Abstract: A process for preparing cyclohexanol and cyclohexanone from cyclohexane includes steps of: (1) non-catalyticly oxidizing cyclohexane with molecular oxygen to obtain an oxidized mixture liquid containing cyclohexyl hydroperoxide (CHHP) as a main product; (2) performing a homogenous catalytic decomposition with an oil-soluble transitional metal compound serving as a catalyst, and serving as a scale inhibitor by 1-hydroxy ethidene-1,1-diphosphonic acid (di)octyl ester, or a combination of 1-hydroxy ethidene-1,1-diphosphonic acid (di)octyl ester and phosphoric acid octyl ester, to decompose the CHHP in the oxidized mixture liquid into cyclohexanol and cyclohexanone; and (3) rectifying to obtain products of the cyclohexanol and the cyclohexanone.
    Type: Application
    Filed: May 17, 2012
    Publication date: April 16, 2015
    Inventor: Zaosheng Xiao
  • Publication number: 20150105590
    Abstract: A process for preparing cyclohexanol and cyclohexanone by cyclohexane oxidation includes steps of: non-catalyticly oxidizing cyclohexane with molecular oxygen in the air to obtain an oxidation mixture containing CHHP as a main product; performing a homogenous catalytic decomposition of the CHHP to obtain cyclohexanol and cyclohexanone; and rectifying to obtain products of the cyclohexanol and the cyclohexanone, wherein the step of performing the homogenous catalytic decomposition involves a homogeneous catalytic decomposition reaction and distillation vessel which removes water via azeotropic rectification to reduce a water content of a decomposition liquid to be below 100 ppm. A device therefor includes the homogeneous catalytic decomposition reaction and distillation vessel for performing the homogenous catalytic decomposition of the CHHP.
    Type: Application
    Filed: May 17, 2012
    Publication date: April 16, 2015
    Inventor: Zaosheng Xiao
  • Publication number: 20150065754
    Abstract: The present invention relates to hydrogenation processes including: contacting a first composition with hydrogen under hydrogenation conditions, in the presence of an eggshell hydrogenation catalyst, wherein the first composition has: (i) greater than about 50 wt % of cyclohexylbenzene, the wt % based upon the total weight of the first composition; and (ii) greater than about 0.3 wt % of cyclohexenylbenzene, the wt % based upon the total weight of the first composition; and thereby obtaining a second composition having less cyclohexenylbenzene than the first composition. Other hydrogenation processes are also described.
    Type: Application
    Filed: April 10, 2013
    Publication date: March 5, 2015
    Inventors: Tan-Jen Chen, Travis A. Reine, Keith H. Kuechler, Terry E. Helton, Jihad M. Dakka
  • Publication number: 20150065753
    Abstract: In a process for separating a mixture comprising cyclohexanone and phenol, at least a portion of the mixture is distilled in the presence of a solvent including at least two alcoholic hydroxyl groups attached to non-adjacent saturated carbon atoms and at least one hemiketal defined by the formula (I) or the formula (II): wherein R1, the same or different at each occurrence, is independently an alkylene group having from 2 to 10 carbon atoms, R2 is an alkylene group having from 4 to 10 carbon atoms, and R3 is hydrogen or the following group: and/or an enol-ether derived from the hemiketal defined by the formula (I) or the formula (II), wherein the total concentration of the hemiketal and the enol-ether, expressed in terms of weight percentage on the basis of the total weight of the feed to the distilling step (a), is at least 0.01%.
    Type: Application
    Filed: April 9, 2013
    Publication date: March 5, 2015
    Inventors: Keith H. Kuechler, Francisco M. Benitez, Krystle J. Chavez, Christopher L. Becker, John L. Heidman, JR.
  • Patent number: 8946484
    Abstract: In a process for producing phenol and cyclohexanone a feed comprising cyclohexylbenzene hydroperoxide and water in an amount from 1 to 15,000 ppm, based upon total weight of feed, is contacted with a cleavage catalyst comprising an aluminosilicate of the FAU type under cleavage conditions effective to convert at least a portion of the cyclohexylbenzene hydroperoxide into phenol and cyclohexanone.
    Type: Grant
    Filed: December 15, 2011
    Date of Patent: February 3, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Kun Wang, Roberto Garcia
  • Patent number: 8940939
    Abstract: A process of oxidizing cyclohexane, comprising feeding cyclohexane, an aqueous hydrogen peroxide solution and optionally an organic solvent into a reaction zone through a feed inlet thereof under the oxidation reaction conditions for contact, and providing all or most of the oxidation product at the reaction zone bottom, wherein a part or all of the packing in the reaction zone is a titanium silicate molecular sieve-containing catalyst. The process of oxidizing cyclohexane according to the present invention carries out the oxidation in the reaction zone, which, firstly, utilizes the latent heat from reaction sufficiently so as to achieve energy-saving; secondly, increases the yield of target product and the availability of oxidizer; and thirdly, allows the separation of the oxidation product from the raw material cyclohexane as the reaction proceeds, such that the cost for subsequent separations can be saved.
    Type: Grant
    Filed: May 2, 2012
    Date of Patent: January 27, 2015
    Assignees: China Petroleum & Chemical Corporation, Research Institute of Petroleum Processing, Sinopec
    Inventors: Min Lin, Chunfeng Shi, Bin Zhu, Yingchun Ru
  • Publication number: 20150005531
    Abstract: In a process for producing phenol, benzene is hydroalkylated with hydrogen in the presence of a catalyst under conditions effective to produce a hydroalkylation reaction product comprising cyclohexylbenzene and cyclohexane. At least a portion of the cyclohexane from said hydroalkylation reaction product is then dehydrogenated to produce a dehydrogenation effluent comprising benzene, toluene and hydrogen. At least a portion of the dehydrogenation effluent is washed with a benzene-containing stream to transfer at least a portion of the toluene from the dehydrogenation effluent to the benzene-containing stream.
    Type: Application
    Filed: November 30, 2012
    Publication date: January 1, 2015
    Applicant: ExxonMobil Chemical Patents Inc.
    Inventors: Christopher L. Becker, James R. Lattner, Keith H. Kuechler, Hari Nair
  • Patent number: 8921604
    Abstract: In a process for producing cyclohexylbenzene, benzene is reacted with cyclohexene in a first reaction zone under conditions effective to produce a reaction product comprising cyclohexylbenzene and at least one polycyclohexylbenzene. At least a portion of the reaction product and a stripping agent comprising at least one C1 to C11 hydrocarbon or hydrogen are then separately supplied to a separation device and separated into at least a first fraction rich in cyclohexylbenzene and a second fraction rich in the at least one polycyclohexylbenzene.
    Type: Grant
    Filed: November 21, 2011
    Date of Patent: December 30, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Christopher L. Becker, James R. Lattner, Charles Morris Smith, Kun Wang
  • Patent number: 8921603
    Abstract: Described herein are compositions having (a) at least 99 wt % cyclohexanone; and (b) 0.1 wppm to 1000 wppm of at least one of cyclohexanedione and hydroxycyclohexanone. The wt % and wppm are based upon the total weight of the composition. The compositions may further comprise 0.1 wppm to 1000 wppm of cyclohexanol.
    Type: Grant
    Filed: August 16, 2011
    Date of Patent: December 30, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Keith H. Kuechler, Francisco M. Benitez
  • Patent number: 8884065
    Abstract: In a process for producing a cycloalkylaromatic compound, an aromatic compound and a cyclic olefin are contacted with a first catalyst under conditions effective to produce a reaction product comprising the cycloalkylaromatic compound and at least one non-fused bicyclic by-product. The at least one non-fused bicyclic by-product is then contacted with a second catalyst under conditions effective to convert at least a portion of the at least one non-fused bicyclic by-product to a converted by-product.
    Type: Grant
    Filed: October 25, 2011
    Date of Patent: November 11, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Kun Wang, Jihad M. Dakka, Stephen Zushma, James R. Lattner, Christopher L. Becker, Tan-Jen Chen
  • Patent number: 8853461
    Abstract: A process for preparing a deperoxidation catalyst comprising chromium as the main catalytic element is described. Also described, is a process for preparing an organic solution of a chromic acid ester. The solution can be used as a catalyst in a deperoxidation of an alkyl peroxide in a process for manufacturing cyclohexanol/cyclohexanone by oxidation of cyclohexane.
    Type: Grant
    Filed: November 18, 2010
    Date of Patent: October 7, 2014
    Assignee: Rhodia Operations
    Inventors: Sandra Chouzier, Serge Veracini, Françoise Igersheim
  • Patent number: 8598388
    Abstract: Process for the preparation of phenol and cyclohexanone which comprises: a. the synthesis of cyclohexylbenzene by the hydro-alkylation of benzene by contact with hydrogen or the alkylation of benzene with cyclohexene using Y zeolites; b. the selective aerobic oxidation of cyclohexylbenzene to the corresponding hydroperoxide catalyzed by N-hydroxy-derivatives in the presence of polar solvents; and c. the scission of the hydroperoxide of cyclohexylbenzene to phenol and cyclohexanone by homogeneous or heterogeneous acid catalysts; characterized in that the synthesis of cyclohexylbenzene takes place in the presence of a catalytic system comprising a Y zeolite and an inorganic ligand wherein the Y zeolite has a crystalline structure with openings consisting of 12 tetrahedra and the inorganic ligand is ?-alumina, and wherein said catalytic composition is characterized by a pore volume, obtained by adding the mesoporosity and macroporosity fractions, greater than or equal to 0.
    Type: Grant
    Filed: June 23, 2010
    Date of Patent: December 3, 2013
    Assignee: Polimeri Europa S.p.A.
    Inventors: Elena Bencini, Cristian Gambarotti, Lucio Melone, Nadia Pastori, Simona Prosperini, Carlo Punta, Francesco Recupero
  • Publication number: 20130225866
    Abstract: Disclosed herein are processes for producing phenol. The processes include oxidizing cyclohexylbenzene to produce an oxidation composition comprising cyclohexyl-1-phenyl-1-hydroperoxide. The cyclohexyl-1-phenyl-1-hydroperoxide in the oxidation composition may undergo a cleavage reaction to produce a cleavage reaction mixture comprising phenol, cyclohexanone and at least one contaminant. The cleavage reaction mixture may be contacted with a basic material to convert at least a portion of the contaminant to a converted contaminant, thereby producing a modified reaction mixture.
    Type: Application
    Filed: August 16, 2011
    Publication date: August 29, 2013
    Applicant: ExxonMobil Chemical Company - Law Technology
    Inventors: Keith Holroyd Kuechler, Francisco Manuel Benitez, Kun Wang, James R. Lattner, Christopher Lynn Becker
  • Publication number: 20130217921
    Abstract: In a process for producing phenol and cyclohexanone, a feed comprising cyclohexylbenzene is oxidized to produce an oxidation reaction product comprising cyclohexyl-1-phenyl-1-hydroperoxide. At least a portion of the oxidation reaction product is then cleaved to produce a cleavage reaction product comprising phenol, cyclohexanone, and at least one contaminant. At least a portion of the cleavage reaction product is contacted with an acidic material to convert at least a portion of the at least one contaminant to a converted contaminant and thereby produce a modified reaction product.
    Type: Application
    Filed: August 16, 2011
    Publication date: August 22, 2013
    Applicant: ExxonMobil Chemical Patents Inc.
    Inventors: Keith H. Kuechler, Francisco M. Benitez
  • Publication number: 20130211036
    Abstract: A process for oxidizing a composition comprising contacting an alkylbenzene of the general formula (I): where R1 and R2 each independently represents hydrogen or an alkyl group having from 1 to 4 carbon atoms, wherein R1 and R2 may be joined to form a cyclic group having from 4 to 10 carbon atoms, the cyclic group being optionally substituted, and R3 represents hydrogen, one or more alkyl groups having from 1 to 4 carbon atoms or a cyclohexyl group; and (ii) about 0.05 wt % to about 5 wt % of phenol, with oxygen in the presence of a catalyst containing a cyclic imide having the general formula (II): wherein X represents an oxygen atom, a hydroxyl group, or an acyloxy group under conditions effective to convert at least a portion of the alkylbenzene to a hydroperoxide.
    Type: Application
    Filed: August 16, 2011
    Publication date: August 15, 2013
    Applicant: ExxonMobil Chemical Company - Law Technology
    Inventors: Jihad M. Dakka, Edmund J. Mozeleski, Charles Morris Smith, Christopher L. Becker, Stephen Zushma
  • Publication number: 20130202522
    Abstract: The invention relates to hydroalkylation processes. In the processes, a hydrogen stream comprising hydrogen and an impurity is treated to reduce the amount of the impurity in the hydrogen stream. The hydrogen is then hydroalkylated with benzene to form at least some cyclohexylbenzene. The processes also relate to treating a benzene stream comprising benzene and an impurity with an adsorbent to reduce the amount of the impurity in the benzene stream. The hydroalkylation processes described herein may be used as part of a process to make phenol.
    Type: Application
    Filed: April 4, 2011
    Publication date: August 8, 2013
    Inventors: Tan-Jen Chen, Teng Xu, Terry Helton, Francisco M. Benitez, Charles M. Smith
  • Publication number: 20130204045
    Abstract: Described herein are compositions having (a) at least 99 wt % cyclohexanone; and (b) 0.1 wppm to 1000 wppm of at least one of cyclohexanedione and hydroxycyclohexanone. The wt % and wppm are based upon the total weight of the composition. The compositions may further comprise 0.1 wppm to 1000 wppm of cyclohexanol.
    Type: Application
    Filed: August 16, 2011
    Publication date: August 8, 2013
    Inventors: Keith Holroyd Kuechler, Francisco Manuel Benitez
  • Publication number: 20130172514
    Abstract: In a process for producing a cycloalkylaromatic compound, an aromatic compound, hydrogen and at least one diluent are supplied to a hydroalkylation reaction zone, such that the weight ratio of the diluent to the aromatic compound supplied to the hydroalkylation reaction zone is at least 1:100. The aromatic compound, hydrogen and the at least one diluent are then contacted under hydroalkylation conditions with a hydroalkylation catalyst in the hydroalkylation reaction zone to produce an effluent comprising a cycloalkylaromatic compound.
    Type: Application
    Filed: June 28, 2011
    Publication date: July 4, 2013
    Applicant: ExxonMobil Chemical Patents Inc.
    Inventors: Teng Xu, Wenyih F. Lai
  • Publication number: 20130116473
    Abstract: The present invention relates to the preparation of oxovinylionol and its O-protected derivatives of the formula I in which R is hydrogen or an OH protecting group, for example a group Si(Ra)3, by reacting a compound of the general formula II in which R has the meanings given above for formula I, i.e. ?-vinyl ionol (formula II, R=hydrogen) or an O-protected derivative thereof (formula II, R?OH protecting group) with an oxidant in the presence of at least one transition metal, where the oxidant comprises at least one oxygen-containing compound which is selected from among hydrogen peroxide and organic hydroperoxides.
    Type: Application
    Filed: November 9, 2012
    Publication date: May 9, 2013
    Applicant: BASF SE
    Inventor: BASF SE
  • Patent number: 8394995
    Abstract: The invention provides a process for the preparation of a carbonyl compound in high efficiency by oxidizing an alcohol. The process for the preparation of a carbonyl compound of the present invention includes a step of oxidizing an alcohol in the presence of a compound of the formula (I) or a derivative or a salt thereof, and an oxidant, wherein R1 and R2 independently represent hydrogen, a halogen, a nitro or acidic group, or an alkyl or alkoxy group, each of which optionally has a substituent, or R1 and R2 combine the two carbon atoms to which they are boned to form an aromatic ring.
    Type: Grant
    Filed: August 29, 2008
    Date of Patent: March 12, 2013
    Assignee: National University Corporation Nagoya University
    Inventors: Kazuaki Ishihara, Muhammet Uyanik, Yukihiro Isogai, Suguru Ohara
  • Publication number: 20120310012
    Abstract: A process for preparing a deperoxidation catalyst comprising chromium as the main catalytic element is described. Also described, is a process for preparing an organic solution of a chromic acid ester. The solution can be used as a catalyst in a deperoxidation of an alkyl peroxide in a process for manufacturing cyclohexanol/cyclohexanone by oxidation of cyclohexane.
    Type: Application
    Filed: November 18, 2010
    Publication date: December 6, 2012
    Applicant: RHODIA OPERATIONS
    Inventors: Sandra Chouzier, Serge Veracini, Françoise Igersheim
  • Publication number: 20120178969
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are contacted under hydroalkylation conditions with a catalyst system comprising a MCM-22 family molecular sieve and at least one hydrogenation metal. The conditions comprise a temperature of about 140° C. to about 175° C., a pressure of about 135 psig to about 175 psig (931 kPag to 1207 kPag), a hydrogen to benzene molar ratio of about 0.30 to about 0.65 and a weight hourly space velocity of benzene of about 0.26 to about 1.05 hr?1.
    Type: Application
    Filed: March 1, 2012
    Publication date: July 12, 2012
    Inventors: Jane C. CHENG, Tan-Jen CHEN, Prasenjeet GHOSH
  • Publication number: 20120157718
    Abstract: Process for the preparation of phenol and cyclohexanone which comprises: a. the synthesis of cyclohexylbenzene by the hydro-alkylation of benzene by contact with hydrogen or the alkylation of benzene with cyclohexene using Y zeolites; b. the selective aerobic oxidation of cyclohexylbenzene to the corresponding hydroperoxide catalyzed by N-hydroxy-derivatives in the presence of polar solvents; and c. the scission of the hydroperoxide of cyclohexylbenzene to phenol and cyclohexanone by homogeneous or heterogeneous acid catalysts; characterized in that the synthesis of cyclohexylbenzene takes place in the presence of a catalytic system comprising a Y zeolite and an inorganic ligand wherein the Y zeolite has a crystalline structure with openings consisting of 12 tetrahedra and the inorganic ligand is ?-alumina, and wherein said catalytic composition is characterized by a pore volume, obtained by adding the mesoporosity and macroporosity fractions, greater than or equal to 0.
    Type: Application
    Filed: June 23, 2010
    Publication date: June 21, 2012
    Applicant: POLIMERI EUROPA S.P.A.
    Inventors: Elena Bencini, Cristian Gambarotti, Lucio Melone, Nadia Pastori, Simona Prosperini, Carlo Punta, Francesco Recupero
  • Patent number: 8163944
    Abstract: The present invention relates to compositions and methods for achieving the efficient allylic oxidation of organic molecules, especially olefins and steroids, under aqueous conditions. The invention concerns the use of dirhodium (II,II) “paddlewheel complexes, and in particular, dirhodium carboximate and tert-butyl hydroperoxide as catalysts for the reaction. The use of aqueous conditions is particularly advantageous in the allylic oxidation of 7-keto steroids, which could not be effectively oxidized using anhydrous methods, and in extending allylic oxidation to enamides and enol ethers.
    Type: Grant
    Filed: October 6, 2008
    Date of Patent: April 24, 2012
    Assignee: University of Maryland College Park
    Inventors: Michael P. Doyle, Arthur J. Catino, Hojae Choi, Jason M. Nichols
  • Patent number: 7956221
    Abstract: The present invention relates to a process for decomposing cyclohexylhydroperoxide into cyclohexanone, said process comprising mixing an organic feed solution comprising cyclohexylhydroperoxide with an aqueous base solution in the absence of a transition metal catalyst resulting in a mixture comprising (i) an aqueous phase and (ii) an organic phase comprising cyclohexanone and cyclohexanol.
    Type: Grant
    Filed: December 16, 2005
    Date of Patent: June 7, 2011
    Assignee: DSM IP Assets B.V.
    Inventor: Imre Toth
  • Publication number: 20110028762
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are fed to at least one reaction zone. The benzene and hydrogen are then contacted in the at least one reaction zone under hydroalkylation conditions with a catalyst system comprising a molecular sieve having an X-ray diffraction pattern including d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstrom, and at least one hydrogenation metal to produce an effluent containing cyclohexylbenzene. The catalyst system has an acid-to-metal molar ratio of from about 75 to about 750.
    Type: Application
    Filed: October 14, 2010
    Publication date: February 3, 2011
    Inventors: Tan-Jen CHEN, Jane C. Cheng, Terry E. Helton, John Scott Buchanan
  • Patent number: 7834217
    Abstract: Disclosed is a method for industrially efficiently producing a corresponding useful oxidation product such as a cycloalkyl hydroperoxide, a cycloalkanol, and/or a cycloalkanone, especially a particularly useful cycloalkanone, from a cycloalkane with a high selectivity in a good yield at low cost. This method is advantageous in respect of energy and process. Specifically, an oxidation product of a cycloalkane is obtained by oxidizing the cycloalkane in a liquid-liquid two phase system using an aqueous solvent in the presence of a nitrogen atom-containing cyclic compound which contains, as its ring constituent, a structure represented by following Formula (I): wherein X represents an oxygen atom or an —OR group, and wherein R represents a hydrogen atom or a hydroxyl-protecting group, and which has a solubility in water at 25° C. of 0.5 g/100 g-H2O or more.
    Type: Grant
    Filed: November 30, 2007
    Date of Patent: November 16, 2010
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takumi Omori, Yasushi Sato
  • Publication number: 20100197971
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are fed to at least one reaction zone. The benzene and hydrogen are then contacted in the at least one reaction zone under hydroalkylation conditions with a catalyst system comprising a molecular sieve having an X-ray diffraction pattern including d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstrom, and at least one hydrogenation metal to produce an effluent containing cyclohexylbenzene. The ratio of the total number of moles of hydrogen fed to said at least one reaction zone to the number of moles of benzene fed to said at least one reaction zone is between 0.4 and 0.9:1.
    Type: Application
    Filed: August 12, 2008
    Publication date: August 5, 2010
    Inventors: Tan-Jen Chen, Francisco M. Benitez, Jane C. Cheng, Jon E. Stanat, John Scott Buchanan