WO2011096993A3 - Dehydrogenation process - Google Patents

Dehydrogenation process Download PDF

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Publication number
WO2011096993A3
WO2011096993A3 PCT/US2010/061012 US2010061012W WO2011096993A3 WO 2011096993 A3 WO2011096993 A3 WO 2011096993A3 US 2010061012 W US2010061012 W US 2010061012W WO 2011096993 A3 WO2011096993 A3 WO 2011096993A3
Authority
WO
WIPO (PCT)
Prior art keywords
cyclohexanone
dehydrogenation
feed
dehydrogenation process
phenol
Prior art date
Application number
PCT/US2010/061012
Other languages
French (fr)
Other versions
WO2011096993A2 (en
WO2011096993A8 (en
Inventor
Teng Xu
Edward A. Lemon
Wenyih Frank Lai
George H. Gamble
Original Assignee
Exxonmobil Chemical Patents Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Exxonmobil Chemical Patents Inc. filed Critical Exxonmobil Chemical Patents Inc.
Priority to CN2010800610233A priority Critical patent/CN102695693A/en
Priority to US13/511,453 priority patent/US20120316365A1/en
Publication of WO2011096993A2 publication Critical patent/WO2011096993A2/en
Publication of WO2011096993A3 publication Critical patent/WO2011096993A3/en
Publication of WO2011096993A8 publication Critical patent/WO2011096993A8/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/041—Mesoporous materials having base exchange properties, e.g. Si/Al-MCM-41
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/041—Mesoporous materials having base exchange properties, e.g. Si/Al-MCM-41
    • B01J29/042—Mesoporous materials having base exchange properties, e.g. Si/Al-MCM-41 containing iron group metals, noble metals or copper
    • B01J29/043—Noble metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • B01J37/0205—Impregnation in several steps
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/74—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition with simultaneous hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
    • C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Abstract

In a process for the dehydrogenation of cyclohexanone to produce phenol, a feed comprising cyclohexanone is contacted with a catalyst comprising an inorganic, crystalline, mesoporous support material and a hydrogenation-dehydrogenation component under dehydrogenation conditions effective to convert at least part of the cyclohexanone in the feed into phenol and hydrogen.
PCT/US2010/061012 2010-02-05 2010-12-17 Dehydrogenation process WO2011096993A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN2010800610233A CN102695693A (en) 2010-02-05 2010-12-17 Dehydrogenation process
US13/511,453 US20120316365A1 (en) 2010-02-05 2010-12-17 Dehydrogenation Process

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US30178010P 2010-02-05 2010-02-05
US61/301,780 2010-02-05

Publications (3)

Publication Number Publication Date
WO2011096993A2 WO2011096993A2 (en) 2011-08-11
WO2011096993A3 true WO2011096993A3 (en) 2011-09-29
WO2011096993A8 WO2011096993A8 (en) 2011-11-17

Family

ID=44120878

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/061012 WO2011096993A2 (en) 2010-02-05 2010-12-17 Dehydrogenation process

Country Status (2)

Country Link
CN (1) CN102695693A (en)
WO (1) WO2011096993A2 (en)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9024078B2 (en) 2010-02-05 2015-05-05 Exxonmobil Chemical Patents Inc. Dehydrogenation process
US9035107B2 (en) 2010-02-05 2015-05-19 Exxonmobil Chemical Patents Inc. Dehydrogenation process
SG191031A1 (en) 2010-12-17 2013-08-30 Exxonmobil Chem Patents Inc Dehydrogenation catalyst and process
SG193427A1 (en) 2011-03-28 2013-10-30 Exxonmobil Chem Patents Inc Dehydrogenation process
US9534104B2 (en) 2013-01-28 2017-01-03 Exxonmobil Chemical Patents Inc. Plasticizer blends and use thereof
US9085669B2 (en) 2013-01-28 2015-07-21 Exxonmobil Chemical Patents Inc. Alkyl aromatic hydroalkylation for the production of plasticizers
BR112015021665A2 (en) * 2013-03-14 2017-07-18 Exxonmobil Chemical Patents Inc mixtures of (methylcyclohexyl) toluene isomers, their production and use in the manufacture of plasticizers
US9725377B2 (en) * 2013-03-14 2017-08-08 Exxonmobil Chemical Patents Inc. Hydroalkylation catalyst and process for use thereof
WO2014159094A1 (en) * 2013-03-14 2014-10-02 Exxonmobil Chemical Patents Inc. Methyl-substituted biphenyl compounds, their production and their use in the manufacture of plasticizers
WO2014159101A1 (en) 2013-03-14 2014-10-02 Exxonmobil Chemical Patents Inc. Methyl-substituted biphenyl compounds, their production and their use in the manufacture of plasticizers
WO2014159106A1 (en) 2013-03-14 2014-10-02 Exxonmobil Chemical Patents Inc. Methyl-substituted biphenyl compounds, their production and their use in the manufacture of plasticizers
BR112015020958A2 (en) 2013-03-14 2017-07-18 Exxonmobil Chemical Patents Inc Substituted methyl biphenyl compounds, their production and use in the manufacture of plasticizers
US9896393B2 (en) 2014-06-13 2018-02-20 Exxonmobil Chemical Patents Inc. Process for preparing dialkylbiphenyl isomer mixtures
EP3180305A1 (en) * 2014-08-15 2017-06-21 ExxonMobil Chemical Patents Inc. Process and system for making cyclohexanone
WO2016025213A1 (en) * 2014-08-15 2016-02-18 Exxonmobil Chemical Patents Inc. Process and system for making cyclohexanone
SG11201700431WA (en) 2014-08-15 2017-02-27 Exxonmobil Chemical Patents Inc Process and system for making cyclohexanone
WO2016025217A1 (en) 2014-08-15 2016-02-18 Exxonmobil Chemical Patents Inc. Process and system for making cyclohexanone
SG11201701764WA (en) 2014-09-30 2017-04-27 Exxonmobil Chemical Patents Inc Process for making cyclohexanone
SG11201701945RA (en) 2014-09-30 2017-04-27 Exxonmobil Chemical Patents Inc Process for making cyclohexanone
US9758447B2 (en) 2014-10-24 2017-09-12 Exxonmobil Chemical Patents Inc. Activation of dehydrogenation catalysts
US9856186B2 (en) 2014-12-19 2018-01-02 Exxonmobil Chemical Patents Inc. Production and use of dialkylbiphenyl isomer mixtures

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0319302A2 (en) * 1987-12-03 1989-06-07 Mitsui Petrochemical Industries, Ltd. Process for dehydrogenating cyclohexenone
WO2001015803A1 (en) * 1999-08-27 2001-03-08 Huntsman Petrochemical Corporation Advances in dehydrogenation catalysis
DE10018724A1 (en) * 2000-04-15 2001-10-25 Inst Brennstoffchemie Und Phys Production of olefins, used in production of e.g. plastics, rubber, detergent, antiknock fuel, aminoacid or vitamin, uses zeolite containing titanium or metal-doped silicon-rich hexagonal mesoporous material for dehydrogenation of alkanes
EP1430949A1 (en) * 2002-12-10 2004-06-23 Haldor Topsoe A/S Process for catalytic dehydrogenation and catalyst therefore
WO2009134514A1 (en) * 2008-05-01 2009-11-05 Exxonmobil Chemical Patents Inc. Process for producing cyclohexanone

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1499878A (en) * 1965-12-08 1967-11-03 Inst Francais Du Petrole Process for the manufacture of phenol by catalytic dehydrogenation of cyclohexanol, cyclohexanone or mixtures thereof
US4021490A (en) 1975-10-14 1977-05-03 Phillips Petroleum Company Process for production of phenol and cyclohexanone
US4019965A (en) 1976-07-20 1977-04-26 Phillips Petroleum Company Separation of phenol, cyclohexanone, and cyclohexylbenzene containing mixtures employing dialkyl and dicycloalkyl phthalates
US4016049A (en) 1976-07-28 1977-04-05 Phillips Petroleum Company Separation of phenol-cyclohexanone azeotrope by extractive distillation with adipic acid diester
US4115204A (en) 1977-07-21 1978-09-19 Phillips Petroleum Company Separation of phenol-, cyclohexanone-, and cyclohexylbenzene-containing mixtures employing an N,N-disubstituted amide
US4115206A (en) 1977-07-21 1978-09-19 Phillips Petroleum Company Separation of phenol-, cyclohexanone-, and cyclohexylbenzene-containing mixtures employing an organic carbonate
US4115205A (en) 1977-07-21 1978-09-19 Phillips Petroleum Company Separation of phenol-, cyclohexanone-, and cyclohexylbenzene-containing mixtures employing an N-substituted lactam
US4115207A (en) 1977-07-27 1978-09-19 Phillips Petroleum Company Separation of phenol-, cyclohexanone-, and cyclohexylbenzene-containing mixtures employing a trisubstituted phosphate
US4167456A (en) 1978-10-06 1979-09-11 Phillips Petroleum Co. Extractive distillation to separate cyclohexylbenzene from phenol-cyclohexanone mixture containing the same
US4201632A (en) 1978-12-20 1980-05-06 Phillips Petroleum Company Separation of phenol-, cyclohexanone-, and cyclohexylbenzene-containing mixtures employing a nitrile as extraction distillation solvent
US4230638A (en) 1979-05-04 1980-10-28 Phillips Petroleum Company Separation of cyclohexylbenzene from a cyclohexylbenzene-cyclohexanone-phenol admixture
US5198203A (en) 1990-01-25 1993-03-30 Mobil Oil Corp. Synthetic mesoporous crystalline material
US5304363A (en) 1990-01-25 1994-04-19 Mobil Oil Corp. Porous materials
US5102643A (en) 1990-01-25 1992-04-07 Mobil Oil Corp. Composition of synthetic porous crystalline material, its synthesis
US5232580A (en) * 1991-06-21 1993-08-03 Mobil Oil Corporation Catalytic process for hydrocarbon cracking using synthetic mesoporous crystalline material
US7285512B2 (en) 2004-08-31 2007-10-23 Exxonmobile Research And Engineering Company Selective hydrodesulfurization catalyst
CA2588134A1 (en) 2004-11-17 2006-06-22 Hyperion Catalysis International, Inc. Method for preparing catalyst supports and supported catalysts from single walled carbon nanotubes
US8247627B2 (en) 2008-04-25 2012-08-21 Exxonmobil Chemical Patents Inc. Process for producing phenol and/or cyclohexanone

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0319302A2 (en) * 1987-12-03 1989-06-07 Mitsui Petrochemical Industries, Ltd. Process for dehydrogenating cyclohexenone
WO2001015803A1 (en) * 1999-08-27 2001-03-08 Huntsman Petrochemical Corporation Advances in dehydrogenation catalysis
DE10018724A1 (en) * 2000-04-15 2001-10-25 Inst Brennstoffchemie Und Phys Production of olefins, used in production of e.g. plastics, rubber, detergent, antiknock fuel, aminoacid or vitamin, uses zeolite containing titanium or metal-doped silicon-rich hexagonal mesoporous material for dehydrogenation of alkanes
EP1430949A1 (en) * 2002-12-10 2004-06-23 Haldor Topsoe A/S Process for catalytic dehydrogenation and catalyst therefore
WO2009134514A1 (en) * 2008-05-01 2009-11-05 Exxonmobil Chemical Patents Inc. Process for producing cyclohexanone

Non-Patent Citations (8)

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Title
AVELINO CORMA: "From Microporous to Mesoporous Molecular Sieve Materials and Their Use in Catalysis", CHEM. REV., vol. 97, 1997, pages 2373 - 2419, XP002656073 *
B. SOLSONA ET AL: "Vanadium Oxide Supported on Mesoporous MCM-41 as Selective Catalyst in the Oxidative Dehydrogenation of Alkanes", JOURNAL OF CATALYST, vol. 203, 2001, pages 443 - 452, XP002656069 *
HAROLD E. SWIFT ET AL: "Metallic Phases and Activities of Nickel-Tin-Silica Catalysts. Dehydrogenation of Cyclohexanone, Cyclohexanol, and cyclohexane", JOURNAL OF CATALYST, vol. 12, 1968, pages 5 - 14, XP002656072 *
M.C. SAMOLADA ET AL: "Catalyst Evaluation for Catalytic Biomass Pyrolysis", ENERGY & FUELS, vol. 14, 2000, pages 1161 - 1167, XP002656075 *
MARIA LEZANSKA ET AL: "Characterization of Cr-MCM-41 and Al, Cr-MCM-41 Mesoporous Catalyst for Gas-Phase Oxidative Dehydrogenation of Cyclohexane", J. PHYS. CHEM. C, vol. 111, 2007, pages 1830 - 1839, XP002656071 *
MITSUO MASAI ET AL: "Dehydrogenation Activity of Nickel-Tin-Silica Catalyst", JOURNAL OF CATALYST, vol. 38, 1975, pages 128 - 134, XP002656076 *
R.B. BORADE ET AL: "Selective dehydrogenation of cyclohexene to benzene using Pd-exchanged alpha-zirconium phosphate", CATALYST LETTERS, vol. 45, 1997, pages 233 - 235, XP002656070 *
SATOSHI KAMIGUCHI ET AL: "Catalytic hydrodehydration of Cyclohexanone, Hydrogenation of 2-Cyclohexen-1-one, and Dehydrogenation of Cyclohexene over a Mo Chloride Cluster with an octahedral Metal Framework", JOURNAL OF CLUSTER SCIENCE, vol. 16, no. 1, 2005, pages 77 - 91, XP002656074 *

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Publication number Publication date
WO2011096993A2 (en) 2011-08-11
WO2011096993A8 (en) 2011-11-17
CN102695693A (en) 2012-09-26

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