RU2011107273A - Прямое и селективное получение ацетальдегида из уксусной кислоты с использованием нанесенного металлического катализатора - Google Patents
Прямое и селективное получение ацетальдегида из уксусной кислоты с использованием нанесенного металлического катализатора Download PDFInfo
- Publication number
- RU2011107273A RU2011107273A RU2011107273/04A RU2011107273A RU2011107273A RU 2011107273 A RU2011107273 A RU 2011107273A RU 2011107273/04 A RU2011107273/04 A RU 2011107273/04A RU 2011107273 A RU2011107273 A RU 2011107273A RU 2011107273 A RU2011107273 A RU 2011107273A
- Authority
- RU
- Russia
- Prior art keywords
- acetic acid
- acetaldehyde
- hydrogen
- selectivity
- consumed
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract 93
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 title claims abstract 42
- 239000003054 catalyst Substances 0.000 title claims abstract 14
- 229910052751 metal Inorganic materials 0.000 title claims abstract 8
- 239000002184 metal Substances 0.000 title claims abstract 8
- 238000000034 method Methods 0.000 claims abstract 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract 14
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 11
- 239000001257 hydrogen Substances 0.000 claims abstract 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract 8
- 239000010949 copper Substances 0.000 claims abstract 7
- 239000010931 gold Substances 0.000 claims abstract 7
- 229910052742 iron Inorganic materials 0.000 claims abstract 7
- 229910052763 palladium Inorganic materials 0.000 claims abstract 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract 5
- 229910052802 copper Inorganic materials 0.000 claims abstract 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims abstract 5
- 229910052737 gold Inorganic materials 0.000 claims abstract 5
- 229910052814 silicon oxide Inorganic materials 0.000 claims abstract 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract 4
- 230000003197 catalytic effect Effects 0.000 claims abstract 4
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052700 potassium Inorganic materials 0.000 claims abstract 3
- 239000011591 potassium Substances 0.000 claims abstract 3
- 239000000377 silicon dioxide Substances 0.000 claims abstract 3
- 239000012159 carrier gas Substances 0.000 claims abstract 2
- 239000007789 gas Substances 0.000 claims abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 3
- 229910017052 cobalt Inorganic materials 0.000 claims 3
- 239000010941 cobalt Substances 0.000 claims 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 3
- 229910052697 platinum Inorganic materials 0.000 claims 3
- 229910052707 ruthenium Inorganic materials 0.000 claims 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 2
- 229910052782 aluminium Inorganic materials 0.000 claims 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 2
- 229910052750 molybdenum Inorganic materials 0.000 claims 2
- 239000011733 molybdenum Substances 0.000 claims 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 2
- 229910052718 tin Inorganic materials 0.000 claims 2
- 235000011056 potassium acetate Nutrition 0.000 claims 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims 1
- 229910052721 tungsten Inorganic materials 0.000 claims 1
- 239000010937 tungsten Substances 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
Classifications
-
- 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
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives 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
- 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
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/06—Acetaldehyde
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/221,135 | 2008-07-31 | ||
| US12/221,135 US7816565B2 (en) | 2008-07-31 | 2008-07-31 | Direct and selective production of acetaldehyde from acetic acid utilizing a supported metal catalyst |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2011107273A true RU2011107273A (ru) | 2012-09-10 |
Family
ID=41354062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2011107273/04A RU2011107273A (ru) | 2008-07-31 | 2009-07-20 | Прямое и селективное получение ацетальдегида из уксусной кислоты с использованием нанесенного металлического катализатора |
Country Status (14)
| Country | Link |
|---|---|
| US (4) | US7816565B2 (enExample) |
| EP (1) | EP2318348A2 (enExample) |
| JP (2) | JP5053458B2 (enExample) |
| KR (1) | KR20110047209A (enExample) |
| CN (1) | CN102143932A (enExample) |
| AR (1) | AR074714A1 (enExample) |
| AU (1) | AU2009277184B2 (enExample) |
| CA (1) | CA2732364A1 (enExample) |
| CO (1) | CO6541516A2 (enExample) |
| IL (1) | IL210947A0 (enExample) |
| RU (1) | RU2011107273A (enExample) |
| TW (1) | TW201012785A (enExample) |
| WO (1) | WO2010014146A2 (enExample) |
| ZA (1) | ZA201100790B (enExample) |
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| US7816565B2 (en) | 2008-07-31 | 2010-10-19 | Celanese International Corporation | Direct and selective production of acetaldehyde from acetic acid utilizing a supported metal catalyst |
| US8546622B2 (en) | 2008-07-31 | 2013-10-01 | Celanese International Corporation | Process for making ethanol from acetic acid using acidic catalysts |
| US8637714B2 (en) | 2008-07-31 | 2014-01-28 | Celanese International Corporation | Process for producing ethanol over catalysts containing platinum and palladium |
| US8680317B2 (en) * | 2008-07-31 | 2014-03-25 | Celanese International Corporation | Processes for making ethyl acetate from acetic acid |
| US8471075B2 (en) | 2008-07-31 | 2013-06-25 | Celanese International Corporation | Processes for making ethanol from acetic acid |
| US8309772B2 (en) * | 2008-07-31 | 2012-11-13 | Celanese International Corporation | Tunable catalyst gas phase hydrogenation of carboxylic acids |
| US8304586B2 (en) | 2010-02-02 | 2012-11-06 | Celanese International Corporation | Process for purifying ethanol |
| GB0817109D0 (en) * | 2008-09-18 | 2008-10-29 | Johnson Matthey Plc | Catalyst and process |
| US8178715B2 (en) * | 2008-12-31 | 2012-05-15 | Celanese International Corporation | Integrated process for the production of vinyl acetate from acetic acid via acetaldehyde |
| US8680321B2 (en) * | 2009-10-26 | 2014-03-25 | Celanese International Corporation | Processes for making ethanol from acetic acid using bimetallic catalysts |
| US8710277B2 (en) * | 2009-10-26 | 2014-04-29 | Celanese International Corporation | Process for making diethyl ether from acetic acid |
| US8747492B2 (en) | 2010-02-02 | 2014-06-10 | Celanese International Corporation | Ethanol/fuel blends for use as motor fuels |
| US8728179B2 (en) | 2010-02-02 | 2014-05-20 | Celanese International Corporation | Ethanol compositions |
| US8541633B2 (en) | 2010-02-02 | 2013-09-24 | Celanese International Corporation | Processes for producing anhydrous ethanol compositions |
| US8668750B2 (en) | 2010-02-02 | 2014-03-11 | Celanese International Corporation | Denatured fuel ethanol compositions for blending with gasoline or diesel fuel for use as motor fuels |
| US8932372B2 (en) | 2010-02-02 | 2015-01-13 | Celanese International Corporation | Integrated process for producing alcohols from a mixed acid feed |
| CN102413921B (zh) | 2010-02-02 | 2016-05-18 | 国际人造丝公司 | 由乙醛生产乙醇的方法 |
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| US8858659B2 (en) * | 2010-02-02 | 2014-10-14 | Celanese International Corporation | Processes for producing denatured ethanol |
| US8680343B2 (en) | 2010-02-02 | 2014-03-25 | Celanese International Corporation | Process for purifying ethanol |
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| US8222466B2 (en) | 2010-02-02 | 2012-07-17 | Celanese International Corporation | Process for producing a water stream from ethanol production |
| US8575403B2 (en) | 2010-05-07 | 2013-11-05 | Celanese International Corporation | Hydrolysis of ethyl acetate in ethanol separation process |
| US8680342B2 (en) | 2010-05-07 | 2014-03-25 | Celanese International Corporation | Process for recovering alcohol produced by hydrogenating an acetic acid feed stream comprising water |
| US8569551B2 (en) | 2010-05-07 | 2013-10-29 | Celanese International Corporation | Alcohol production process integrating acetic acid feed stream comprising water from carbonylation process |
| US8754267B2 (en) | 2010-05-07 | 2014-06-17 | Celanese International Corporation | Process for separating acetaldehyde from ethanol-containing mixtures |
| WO2012148509A1 (en) | 2011-04-26 | 2012-11-01 | Celanese International Corporation | Process for producing ethanol using a stacked bed reactor |
| US9272970B2 (en) | 2010-07-09 | 2016-03-01 | Celanese International Corporation | Hydrogenolysis of ethyl acetate in alcohol separation processes |
| US8710279B2 (en) | 2010-07-09 | 2014-04-29 | Celanese International Corporation | Hydrogenolysis of ethyl acetate in alcohol separation processes |
| US8664454B2 (en) | 2010-07-09 | 2014-03-04 | Celanese International Corporation | Process for production of ethanol using a mixed feed using copper containing catalyst |
| FR2972450B1 (fr) * | 2011-03-07 | 2013-04-12 | Rhodia Operations | Preparation d'ethers de (poly)glycerol |
| KR101269857B1 (ko) | 2011-04-14 | 2013-06-07 | 서강대학교산학협력단 | 알킨으로부터 알켄의 선택적 수소화 반응용 촉매 |
| TW201302684A (zh) | 2011-04-26 | 2013-01-16 | Celanese Int Corp | 由醋酸進料及再循環醋酸乙酯進料生產乙醇之製程 |
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| JP6650351B2 (ja) * | 2016-06-21 | 2020-02-19 | 株式会社ダイセル | 触媒、触媒の製造方法、及びアルデヒド類の製造方法 |
| JP6758113B2 (ja) * | 2016-07-12 | 2020-09-23 | 株式会社ダイセル | 固体触媒、及びアルデヒド類の製造方法 |
| JP2018149507A (ja) * | 2017-03-14 | 2018-09-27 | 株式会社ダイセル | 触媒及びアルデヒド類の製造方法 |
| JP2019107590A (ja) * | 2017-12-15 | 2019-07-04 | 株式会社ダイセル | 触媒、アルデヒド類および／またはアルコール類の製造方法 |
| JP7098434B2 (ja) * | 2017-12-20 | 2022-07-11 | 株式会社ダイセル | 固体触媒、及びアルデヒド類の製造方法 |
| JP7098435B2 (ja) * | 2018-06-22 | 2022-07-11 | 株式会社ダイセル | 固体触媒、及びアルデヒド類の製造方法 |
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-
2008
- 2008-07-31 US US12/221,135 patent/US7816565B2/en not_active Expired - Fee Related
-
2009
- 2009-07-20 WO PCT/US2009/004187 patent/WO2010014146A2/en not_active Ceased
- 2009-07-20 EP EP09788947A patent/EP2318348A2/en not_active Withdrawn
- 2009-07-20 CA CA2732364A patent/CA2732364A1/en not_active Abandoned
- 2009-07-20 RU RU2011107273/04A patent/RU2011107273A/ru not_active Application Discontinuation
- 2009-07-20 KR KR1020117004664A patent/KR20110047209A/ko not_active Withdrawn
- 2009-07-20 AU AU2009277184A patent/AU2009277184B2/en not_active Ceased
- 2009-07-20 JP JP2011521093A patent/JP5053458B2/ja not_active Expired - Fee Related
- 2009-07-20 CN CN2009801340830A patent/CN102143932A/zh active Pending
- 2009-07-31 AR ARP090102963A patent/AR074714A1/es not_active Application Discontinuation
- 2009-07-31 TW TW098125963A patent/TW201012785A/zh unknown
-
2010
- 2010-09-16 US US12/883,989 patent/US7994368B2/en not_active Expired - Fee Related
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2011
- 2011-01-30 IL IL210947A patent/IL210947A0/en unknown
- 2011-01-31 ZA ZA2011/00790A patent/ZA201100790B/en unknown
- 2011-06-17 US US13/163,236 patent/US8227644B2/en not_active Expired - Fee Related
- 2011-07-19 CO CO11090420A patent/CO6541516A2/es not_active Application Discontinuation
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2012
- 2012-03-08 JP JP2012051874A patent/JP5108980B2/ja not_active Expired - Fee Related
- 2012-06-22 US US13/530,745 patent/US8461395B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2732364A1 (en) | 2010-02-04 |
| US7994368B2 (en) | 2011-08-09 |
| JP2012153698A (ja) | 2012-08-16 |
| US20100029993A1 (en) | 2010-02-04 |
| AU2009277184A1 (en) | 2010-02-04 |
| IL210947A0 (en) | 2011-04-28 |
| JP5108980B2 (ja) | 2012-12-26 |
| US8461395B2 (en) | 2013-06-11 |
| AU2009277184A2 (en) | 2011-02-24 |
| US20110251435A1 (en) | 2011-10-13 |
| US8227644B2 (en) | 2012-07-24 |
| JP2011529494A (ja) | 2011-12-08 |
| US7816565B2 (en) | 2010-10-19 |
| AU2009277184B2 (en) | 2012-12-06 |
| JP5053458B2 (ja) | 2012-10-17 |
| KR20110047209A (ko) | 2011-05-06 |
| EP2318348A2 (en) | 2011-05-11 |
| US20120283480A1 (en) | 2012-11-08 |
| AR074714A1 (es) | 2011-02-09 |
| ZA201100790B (en) | 2012-04-25 |
| WO2010014146A2 (en) | 2010-02-04 |
| WO2010014146A3 (en) | 2010-05-06 |
| TW201012785A (en) | 2010-04-01 |
| CO6541516A2 (es) | 2012-10-16 |
| US20110004026A1 (en) | 2011-01-06 |
| CN102143932A (zh) | 2011-08-03 |
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