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WO2011056597A3 - Process for making ethanol from acetic acid using acidic catalysts - Google Patents

Process for making ethanol from acetic acid using acidic catalysts Download PDF

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Publication number
WO2011056597A3
WO2011056597A3 PCT/US2010/054136 US2010054136W WO2011056597A3 WO 2011056597 A3 WO2011056597 A3 WO 2011056597A3 US 2010054136 W US2010054136 W US 2010054136W WO 2011056597 A3 WO2011056597 A3 WO 2011056597A3
Authority
WO
WIPO (PCT)
Prior art keywords
acetic acid
ethanol
acidic catalysts
making ethanol
acidic support
Prior art date
Application number
PCT/US2010/054136
Other languages
French (fr)
Other versions
WO2011056597A2 (en
Inventor
Radmila Jevtic
Victor J. Johnston
R. Jay Warner
Heiko Weiner
Original Assignee
Celanese International Corporation
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
Priority claimed from US12/588,727 external-priority patent/US8309772B2/en
Priority claimed from US12/699,024 external-priority patent/US8680317B2/en
Priority claimed from US12/698,947 external-priority patent/US8471075B2/en
Priority claimed from US12/852,227 external-priority patent/US8309773B2/en
Priority claimed from US12/852,269 external-priority patent/US8304586B2/en
Priority to BR112012009824A priority Critical patent/BR112012009824A2/en
Priority to CN201080003928.5A priority patent/CN102307657B/en
Priority to AU2010315554A priority patent/AU2010315554A1/en
Priority to NZ599463A priority patent/NZ599463A/en
Priority to JP2012535458A priority patent/JP2013508424A/en
Application filed by Celanese International Corporation filed Critical Celanese International Corporation
Priority to KR1020127013286A priority patent/KR20120086717A/en
Priority to MX2012004842A priority patent/MX2012004842A/en
Priority to RU2012121872/04A priority patent/RU2012121872A/en
Priority to EP10773795A priority patent/EP2493610A2/en
Priority to CA2778959A priority patent/CA2778959A1/en
Priority to PCT/US2010/054136 priority patent/WO2011056597A2/en
Publication of WO2011056597A2 publication Critical patent/WO2011056597A2/en
Publication of WO2011056597A3 publication Critical patent/WO2011056597A3/en
Priority to ZA2012/02850A priority patent/ZA201202850B/en
Priority to IL219399A priority patent/IL219399A0/en

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    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/002—Mixed oxides other than spinels, e.g. perovskite
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
    • B01J21/04—Alumina
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/063—Titanium; Oxides or hydroxides thereof
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/12—Silica and alumina
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
    • B01J23/622—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead
    • B01J23/626—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead with tin
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/656—Manganese, technetium or rhenium
    • B01J23/6567—Rhenium
    • 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
    • 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
    • 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
    • B01J37/0207—Pretreatment of the support
    • 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
    • B01J37/08—Heat treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/94—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/02—Monohydroxylic acyclic alcohols
    • C07C31/08—Ethanol
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/16—Clays or other mineral silicates
    • 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
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

A process for selective formation of ethanol from acetic acid by hydrogenating acetic acid in the presence of a catalyst comprises a first metal on an acidic support. The acidic support may comprise an acidic support material or may comprise an support having an acidic support modifier. The catalyst may be used alone to produced ethanol via hydrogenation or in combination with another catalyst. In addition, the crude ethanol product is separated to obtain ethanol.
PCT/US2010/054136 2009-10-26 2010-10-26 Process for making ethanol from acetic acid using acidic catalysts WO2011056597A2 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
MX2012004842A MX2012004842A (en) 2009-10-26 2010-10-26 Process for making ethanol from acetic acid using acidic catalysts.
RU2012121872/04A RU2012121872A (en) 2009-10-26 2010-10-26 METHOD FOR PRODUCING ETHANOL FROM ACETIC ACID USING ACID CATALYSTS
CN201080003928.5A CN102307657B (en) 2009-10-26 2010-10-26 Process for making ethanol from acetic acid using acidic catalysts
PCT/US2010/054136 WO2011056597A2 (en) 2009-10-26 2010-10-26 Process for making ethanol from acetic acid using acidic catalysts
CA2778959A CA2778959A1 (en) 2009-10-26 2010-10-26 Process for making ethanol from acetic acid using acidic catalysts
EP10773795A EP2493610A2 (en) 2009-10-26 2010-10-26 Process for making ethanol from acetic acid using acidic catalysts
AU2010315554A AU2010315554A1 (en) 2009-10-26 2010-10-26 Process for making ethanol from acetic acid using acidic catalysts
NZ599463A NZ599463A (en) 2009-10-26 2010-10-26 Process for making ethanol from acetic acid using acidic catalysts
JP2012535458A JP2013508424A (en) 2009-10-26 2010-10-26 Method for producing ethanol from acetic acid using acidic catalyst
BR112012009824A BR112012009824A2 (en) 2009-10-26 2010-10-26 process for the manufacture of ethanol from acetic acid using acid catalysts
KR1020127013286A KR20120086717A (en) 2009-10-26 2010-10-26 Process for making ethanol from acetic acid using acidic catalysts
ZA2012/02850A ZA201202850B (en) 2009-10-26 2012-04-18 Process for making ethanol from acetic acid using acidic catalysts
IL219399A IL219399A0 (en) 2009-10-26 2012-04-24 Process for making ethanol from acetic acid using acidic catalysts

Applications Claiming Priority (17)

Application Number Priority Date Filing Date Title
US12/588,727 2009-10-26
US12/588,727 US8309772B2 (en) 2008-07-31 2009-10-26 Tunable catalyst gas phase hydrogenation of carboxylic acids
US30081510P 2010-02-02 2010-02-02
US12/698,947 US8471075B2 (en) 2008-07-31 2010-02-02 Processes for making ethanol from acetic acid
US12/699,024 2010-02-02
US61/300,815 2010-02-02
US12/699,024 US8680317B2 (en) 2008-07-31 2010-02-02 Processes for making ethyl acetate from acetic acid
US12/698,947 2010-02-02
US33269610P 2010-05-07 2010-05-07
US33269910P 2010-05-07 2010-05-07
US61/332,699 2010-05-07
US61/332,696 2010-05-07
US12/852,227 2010-08-06
US12/852,269 US8304586B2 (en) 2010-02-02 2010-08-06 Process for purifying ethanol
US12/852,227 US8309773B2 (en) 2010-02-02 2010-08-06 Process for recovering ethanol
US12/852,269 2010-08-06
PCT/US2010/054136 WO2011056597A2 (en) 2009-10-26 2010-10-26 Process for making ethanol from acetic acid using acidic catalysts

Publications (2)

Publication Number Publication Date
WO2011056597A2 WO2011056597A2 (en) 2011-05-12
WO2011056597A3 true WO2011056597A3 (en) 2011-07-14

Family

ID=56291204

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/054136 WO2011056597A2 (en) 2009-10-26 2010-10-26 Process for making ethanol from acetic acid using acidic catalysts

Country Status (12)

Country Link
EP (1) EP2493610A2 (en)
JP (1) JP2013508424A (en)
KR (1) KR20120086717A (en)
CN (1) CN102307657B (en)
AU (1) AU2010315554A1 (en)
BR (1) BR112012009824A2 (en)
CA (1) CA2778959A1 (en)
MX (1) MX2012004842A (en)
NZ (1) NZ599463A (en)
RU (1) RU2012121872A (en)
WO (1) WO2011056597A2 (en)
ZA (1) ZA201202850B (en)

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US9073816B2 (en) 2011-04-26 2015-07-07 Celanese International Corporation Reducing ethyl acetate concentration in recycle streams for ethanol production processes
US8440866B2 (en) 2011-08-03 2013-05-14 Celanese International Corporation Process for separating ethanol having low acid
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CN103373899B (en) * 2012-04-27 2016-01-06 上海浦景化工技术股份有限公司 The device and method of a kind of acetic acid or acetic ester catalytic hydrogenation reaction ethanol
CN103570495B (en) * 2012-07-25 2016-02-17 上海浦景化工技术股份有限公司 The device and method of a kind of multistage acetic acid or acetic ester shortening ethanol
CN103664524B (en) * 2012-09-05 2016-01-13 中国石油化工股份有限公司 The method of 1,4 cyclohexanedicarboxylic acid Hydrogenation 1,4 cyclohexane dimethanol
US9834491B2 (en) * 2013-03-20 2017-12-05 Cj Cheiljedang Corporation Method for producing bio-based homoserine lactone and bio-based organic acid from O-acyl homoserine produced by microorganisms
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JP2016026864A (en) * 2014-06-25 2016-02-18 積水化学工業株式会社 Catalyst for synthesis of ethyl acetate, device of producing ethyl acetate and method for producing ethyl acetate
CN104307557B (en) * 2014-09-19 2016-08-17 东营海纳新材料有限公司 A kind of methyl difluoroacetate Hydrogenation is for the preparation method of the catalyst of difluoroethanol
WO2016175747A1 (en) * 2015-04-27 2016-11-03 Celanese International Corporation Hydrogenation catalysts comprising a mixed oxide having bismuth and process for producing ethanol
JP2019107590A (en) * 2017-12-15 2019-07-04 株式会社ダイセル Catalyst and process for producing aldehydes and/or alcohols
EP4444684A1 (en) 2021-12-08 2024-10-16 Linde GmbH Process and plant for producing one or more hydrocarbons
CN114939414A (en) * 2022-06-23 2022-08-26 山东亮剑环保新材料有限公司 Preparation method of supported copper oxide catalyst

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WO2010056299A1 (en) * 2008-11-14 2010-05-20 Celanese International Corporation Integrated process for the production of vinyl acetate from acetic acid via ethylene

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EP2493610A2 (en) 2012-09-05
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WO2011056597A2 (en) 2011-05-12
JP2013508424A (en) 2013-03-07
ZA201202850B (en) 2013-06-26
AU2010315554A1 (en) 2012-05-17
KR20120086717A (en) 2012-08-03
BR112012009824A2 (en) 2016-11-22
MX2012004842A (en) 2012-05-29
RU2012121872A (en) 2013-12-10

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