TW201012785A - Direct and selective production of acetaldehyde from acetic acid utilizing a supported metal catalyst - Google Patents
Direct and selective production of acetaldehyde from acetic acid utilizing a supported metal catalyst Download PDFInfo
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- TW201012785A TW201012785A TW098125963A TW98125963A TW201012785A TW 201012785 A TW201012785 A TW 201012785A TW 098125963 A TW098125963 A TW 098125963A TW 98125963 A TW98125963 A TW 98125963A TW 201012785 A TW201012785 A TW 201012785A
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- Prior art keywords
- catalyst
- iron
- weight
- acetic acid
- tin
- Prior art date
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 352
- 239000003054 catalyst Substances 0.000 title claims abstract description 215
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 229910052751 metal Inorganic materials 0.000 title claims description 61
- 239000002184 metal Substances 0.000 title claims description 61
- 238000004519 manufacturing process Methods 0.000 title abstract description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 227
- 238000000034 method Methods 0.000 claims abstract description 127
- 229910052742 iron Inorganic materials 0.000 claims abstract description 107
- 238000006243 chemical reaction Methods 0.000 claims abstract description 72
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 22
- 239000011135 tin Substances 0.000 claims description 56
- 229910052718 tin Inorganic materials 0.000 claims description 53
- 239000007789 gas Substances 0.000 claims description 52
- 239000010949 copper Substances 0.000 claims description 46
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 43
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 40
- 238000011068 loading method Methods 0.000 claims description 35
- 238000005984 hydrogenation reaction Methods 0.000 claims description 34
- 229910052802 copper Inorganic materials 0.000 claims description 32
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 27
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000004575 stone Substances 0.000 claims description 24
- 229910000420 cerium oxide Inorganic materials 0.000 claims description 22
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 22
- 229910052707 ruthenium Inorganic materials 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- 229910052763 palladium Inorganic materials 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 16
- -1 knot Chemical compound 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 239000010931 gold Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 229910001925 ruthenium oxide Inorganic materials 0.000 claims description 13
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical group O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims description 13
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052737 gold Inorganic materials 0.000 claims description 12
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 11
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 11
- 230000003197 catalytic effect Effects 0.000 claims description 11
- 229910052797 bismuth Inorganic materials 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 229910017052 cobalt Inorganic materials 0.000 claims description 8
- 239000010941 cobalt Substances 0.000 claims description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 8
- 235000011056 potassium acetate Nutrition 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 150000002739 metals Chemical class 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims description 5
- 239000010948 rhodium Substances 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000012159 carrier gas Substances 0.000 claims description 4
- 239000011733 molybdenum Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 238000002309 gasification Methods 0.000 claims description 3
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- 239000001307 helium Substances 0.000 claims description 3
- 235000003642 hunger Nutrition 0.000 claims description 3
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- 238000005121 nitriding Methods 0.000 claims 2
- SHXWCVYOXRDMCX-UHFFFAOYSA-N 3,4-methylenedioxymethamphetamine Chemical compound CNC(C)CC1=CC=C2OCOC2=C1 SHXWCVYOXRDMCX-UHFFFAOYSA-N 0.000 claims 1
- 206010020466 Hunger Diseases 0.000 claims 1
- 241000282320 Panthera leo Species 0.000 claims 1
- 241000239226 Scorpiones Species 0.000 claims 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims 1
- 238000009396 hybridization Methods 0.000 claims 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 claims 1
- 239000004576 sand Substances 0.000 claims 1
- 239000013589 supplement Substances 0.000 claims 1
- 239000010936 titanium Substances 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 7
- 239000000377 silicon dioxide Substances 0.000 abstract description 3
- 239000012808 vapor phase Substances 0.000 abstract 2
- 238000004817 gas chromatography Methods 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
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- 238000009826 distribution Methods 0.000 description 7
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- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- WDZVNNYQBQRJRX-UHFFFAOYSA-K gold(iii) hydroxide Chemical compound O[Au](O)O WDZVNNYQBQRJRX-UHFFFAOYSA-K 0.000 description 6
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- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 5
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
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- 229910052757 nitrogen Inorganic materials 0.000 description 4
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- 239000000052 vinegar Substances 0.000 description 4
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- NGCDGPPKVSZGRR-UHFFFAOYSA-J 1,4,6,9-tetraoxa-5-stannaspiro[4.4]nonane-2,3,7,8-tetrone Chemical compound [Sn+4].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O NGCDGPPKVSZGRR-UHFFFAOYSA-J 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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)
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| 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 |
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| TW201012785A true TW201012785A (en) | 2010-04-01 |
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| TW098125963A TW201012785A (en) | 2008-07-31 | 2009-07-31 | Direct and selective production of acetaldehyde from acetic acid utilizing a supported metal catalyst |
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| US8501652B2 (en) * | 2008-07-31 | 2013-08-06 | Celanese International Corporation | Catalysts for making ethanol from acetic acid |
| US7863489B2 (en) | 2008-07-31 | 2011-01-04 | Celanese International Corporation | Direct and selective production of ethanol from acetic acid utilizing a platinum/tin catalyst |
| 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 |
| US8344186B2 (en) | 2010-02-02 | 2013-01-01 | Celanese International Corporation | Processes for producing ethanol from acetaldehyde |
| 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 |
| US8460405B2 (en) | 2010-02-02 | 2013-06-11 | Celanese International Corporation | Ethanol compositions |
| 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 |
| US8754268B2 (en) | 2011-04-26 | 2014-06-17 | Celanese International Corporation | Process for removing water from alcohol mixtures |
| US9073816B2 (en) | 2011-04-26 | 2015-07-07 | Celanese International Corporation | Reducing ethyl acetate concentration in recycle streams for ethanol production processes |
| US8592635B2 (en) | 2011-04-26 | 2013-11-26 | Celanese International Corporation | Integrated ethanol production by extracting halides from acetic acid |
| US8895786B2 (en) | 2011-08-03 | 2014-11-25 | Celanese International Corporation | Processes for increasing alcohol production |
| US8829253B2 (en) | 2011-08-19 | 2014-09-09 | Celanese International Corporation | Integrated process for producing ethanol from methanol |
| US8853466B2 (en) | 2011-08-19 | 2014-10-07 | Celanese International Corporation | Integrated process for producing ethanol from methanol |
| US8853467B2 (en) | 2011-08-19 | 2014-10-07 | Celanese International Corporation | Integrated process for producing ethanol |
| US8907142B2 (en) | 2011-12-29 | 2014-12-09 | Celanese International Corporation | Process for promoting catalyst activity for ethyl acetate conversion |
| US9353034B2 (en) | 2012-02-07 | 2016-05-31 | Celanese International Corporation | Hydrogenation process with reduced residence time for vapor phase reactants |
| US8729311B2 (en) * | 2012-02-10 | 2014-05-20 | Celanese International Corporaton | Catalysts for converting acetic acid to acetone |
| US8729317B2 (en) | 2012-02-15 | 2014-05-20 | Celanese International Corporation | Ethanol manufacturing process over catalyst with cesium and support comprising tungsten or oxides thereof |
| US8802903B2 (en) | 2012-03-13 | 2014-08-12 | Celanese International Corporation | Stacked bed reactor with diluents for producing ethanol |
| US9073042B2 (en) | 2012-03-14 | 2015-07-07 | Celanese International Corporation | Acetic acid hydrogenation over a group VIII metal calcined catalyst having a secondary promoter |
| CN102658165B (zh) * | 2012-04-06 | 2014-11-05 | 华东理工大学 | 乙酸气相加氢制备乙醇的催化剂及其制备方法 |
| US8853469B2 (en) | 2012-11-20 | 2014-10-07 | Celanese International Corporation | Combined column for separating products of different hydrogenation reactors |
| WO2014119185A1 (ja) * | 2013-01-30 | 2014-08-07 | 株式会社ダイセル | アセトアルデヒドの製造方法 |
| DE102013106787A1 (de) | 2013-06-28 | 2014-12-31 | Oxea Gmbh | Verfahren zur Herstellung von n-Butanderivaten |
| DE102013106790A1 (de) | 2013-06-28 | 2014-12-31 | Oxea Gmbh | Verfahren zur Herstellung von 1,3-Butandiol |
| JP6405367B2 (ja) * | 2014-04-10 | 2018-10-17 | 株式会社ダイセル | アセトアルデヒドの製造方法 |
| JP6442484B2 (ja) * | 2014-04-22 | 2018-12-19 | 株式会社ダイセル | アルデヒド類製造用固体触媒、及びアルデヒド類の製造方法 |
| WO2015166706A1 (ja) * | 2014-04-28 | 2015-11-05 | 株式会社ダイセル | 酢酸及びアセトアルデヒドの製造方法 |
| CN104162446A (zh) * | 2014-08-11 | 2014-11-26 | 华东理工大学 | 用于乙酸加氢制备乙醛的催化剂的制备方法 |
| JP6360801B2 (ja) * | 2015-02-19 | 2018-07-18 | 株式会社ダイセル | 触媒、アルデヒド類及び／又はアルコール類の製造方法 |
| JP6480835B2 (ja) * | 2015-09-02 | 2019-03-13 | 株式会社ダイセル | 固体触媒、固体触媒の製造方法、及びアセトアルデヒドの製造方法 |
| CN105478120B (zh) * | 2015-11-18 | 2017-12-15 | 河南理工大学 | 一种赤泥基铁系催化剂的制备方法及其在甲烷裂解制氢中的应用 |
| 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 |
| CN113198521B (zh) * | 2021-04-30 | 2023-04-07 | 江苏常青树新材料科技股份有限公司 | 一种usy分子筛催化剂的制备方法、及该催化剂在制备二乙烯苯中的应用 |
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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
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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
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- 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 |
| RU2011107273A (ru) | 2012-09-10 |
| 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 |
| CO6541516A2 (es) | 2012-10-16 |
| US20110004026A1 (en) | 2011-01-06 |
| CN102143932A (zh) | 2011-08-03 |
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