JP2013508423A5 - - Google Patents
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- Publication number
- JP2013508423A5 JP2013508423A5 JP2012535457A JP2012535457A JP2013508423A5 JP 2013508423 A5 JP2013508423 A5 JP 2013508423A5 JP 2012535457 A JP2012535457 A JP 2012535457A JP 2012535457 A JP2012535457 A JP 2012535457A JP 2013508423 A5 JP2013508423 A5 JP 2013508423A5
- Authority
- JP
- Japan
- Prior art keywords
- platinum
- group
- tin
- catalyst
- acetic acid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 190
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 144
- 238000000034 method Methods 0.000 claims description 138
- 229910052697 platinum Inorganic materials 0.000 claims description 93
- 229910052718 tin Inorganic materials 0.000 claims description 88
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 87
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 56
- 239000003054 catalyst Substances 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 235000012241 calcium silicate Nutrition 0.000 claims description 19
- 229910052918 calcium silicate Inorganic materials 0.000 claims description 19
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 claims description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000003607 modifier Substances 0.000 claims description 18
- 239000002243 precursor Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000007789 gas Substances 0.000 claims description 15
- 239000012808 vapor phase Substances 0.000 claims description 13
- 238000005984 hydrogenation reaction Methods 0.000 claims description 12
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 11
- 229910052791 calcium Inorganic materials 0.000 claims description 11
- 239000011575 calcium Substances 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 229910052725 zinc Inorganic materials 0.000 claims description 11
- 239000011701 zinc Substances 0.000 claims description 11
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052749 magnesium Inorganic materials 0.000 claims description 10
- 239000011777 magnesium Substances 0.000 claims description 10
- 239000000377 silicon dioxide Substances 0.000 claims description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 8
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229910052702 rhenium Inorganic materials 0.000 claims description 4
- 239000011787 zinc oxide Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 4
- 239000000463 material Substances 0.000 claims 3
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 2
- 229910002804 graphite Inorganic materials 0.000 claims 2
- 239000010439 graphite Substances 0.000 claims 2
- 239000000395 magnesium oxide Substances 0.000 claims 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 239000002028 Biomass Substances 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 1
- 239000003345 natural gas Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- XSMMCTCMFDWXIX-UHFFFAOYSA-N zinc silicate Chemical compound [Zn+2].[O-][Si]([O-])=O XSMMCTCMFDWXIX-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 12
- 239000000378 calcium silicate Substances 0.000 description 7
- 235000014692 zinc oxide Nutrition 0.000 description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 235000012255 calcium oxide Nutrition 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 235000012245 magnesium oxide Nutrition 0.000 description 3
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/588,727 US8309772B2 (en) | 2008-07-31 | 2009-10-26 | Tunable catalyst gas phase hydrogenation of carboxylic acids |
| US12/588,727 | 2009-10-26 | ||
| PCT/US2010/054134 WO2011056595A1 (en) | 2009-10-26 | 2010-10-26 | Catalyst for the production of ethanol by hydrogenation of acetic acid comprising platinum -tin on silicaceous support |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013508423A JP2013508423A (ja) | 2013-03-07 |
| JP2013508423A5 true JP2013508423A5 (enExample) | 2013-12-12 |
| JP5775087B2 JP5775087B2 (ja) | 2015-09-09 |
Family
ID=46506679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012535457A Expired - Fee Related JP5775087B2 (ja) | 2009-10-26 | 2010-10-26 | 酢酸の還元によってエタノールを製造する方法 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP2493609A1 (enExample) |
| JP (1) | JP5775087B2 (enExample) |
| CN (1) | CN102300635B (enExample) |
| AU (1) | AU2010315552B2 (enExample) |
| BR (1) | BR112012009770A2 (enExample) |
| CA (1) | CA2778957A1 (enExample) |
| IL (1) | IL219400A0 (enExample) |
| MX (1) | MX2012004841A (enExample) |
| RU (1) | RU2549893C2 (enExample) |
| WO (1) | WO2011056595A1 (enExample) |
| ZA (1) | ZA201202847B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9079172B2 (en) | 2012-03-13 | 2015-07-14 | Celanese International Corporation | Promoters for cobalt-tin catalysts for reducing alkanoic acids |
| BR112014015080A8 (pt) * | 2011-12-29 | 2017-06-13 | Celanese Int Corp | catalisador de cobalto e estanho para produzir etanol |
| US9333496B2 (en) | 2012-02-29 | 2016-05-10 | Celanese International Corporation | Cobalt/tin catalyst for producing ethanol |
| US8865609B2 (en) * | 2012-01-06 | 2014-10-21 | Celanese International Corporation | Hydrogenation catalysts |
| US9079851B2 (en) * | 2012-02-01 | 2015-07-14 | Greenyug, Llc | Ethyl acetate production |
| US8927786B2 (en) | 2012-03-13 | 2015-01-06 | Celanese International Corporation | Ethanol manufacturing process over catalyst having improved radial crush strength |
| 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 |
| CN104107701B (zh) * | 2013-04-16 | 2016-08-03 | 中国石油化工股份有限公司 | 高活性Pt基催化剂、制备方法及其用途 |
| 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 |
| CN103331158B (zh) * | 2013-07-15 | 2017-08-25 | 上海华谊（集团）公司 | 一种醋酸加氢制乙醇的催化剂及制备方法 |
| CN111359618B (zh) * | 2020-04-23 | 2022-10-25 | 上海亚铂化工科技有限公司 | 催化剂及其制备方法和应用以及催化酯加氢反应的方法 |
| EP4549622A1 (en) | 2023-10-31 | 2025-05-07 | Basf Se | Hydrogenation of carbonyl compounds using hydrogen with low deuterium content |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8509530D0 (en) | 1985-04-13 | 1985-05-15 | Bp Chem Int Ltd | Hydrogenation of carboxylic acids |
| GB8707595D0 (en) | 1987-03-31 | 1987-05-07 | British Petroleum Co Plc | Chemical process |
| US5149680A (en) | 1987-03-31 | 1992-09-22 | The British Petroleum Company P.L.C. | Platinum group metal alloy catalysts for hydrogenation of carboxylic acids and their anhydrides to alcohols and/or esters |
| US5821111A (en) | 1994-03-31 | 1998-10-13 | Bioengineering Resources, Inc. | Bioconversion of waste biomass to useful products |
| USRE35377E (en) | 1993-05-27 | 1996-11-12 | Steinberg; Meyer | Process and apparatus for the production of methanol from condensed carbonaceous material |
| DE19720657A1 (de) * | 1997-05-16 | 1998-11-19 | Basf Ag | Verfahren zur Herstellung von aliphatischen Alkoholen |
| JP3780669B2 (ja) * | 1997-11-17 | 2006-05-31 | 三菱化学株式会社 | アルデヒド類及び、又はアルコール類の製造方法 |
| JP3911955B2 (ja) * | 1999-04-28 | 2007-05-09 | 三菱化学株式会社 | ルテニウム−スズ系担持触媒の製造方法。 |
| US6232352B1 (en) | 1999-11-01 | 2001-05-15 | Acetex Limited | Methanol plant retrofit for acetic acid manufacture |
| US6657078B2 (en) | 2001-02-07 | 2003-12-02 | Celanese International Corporation | Low energy carbonylation process |
| US6685754B2 (en) | 2001-03-06 | 2004-02-03 | Alchemix Corporation | Method for the production of hydrogen-containing gaseous mixtures |
| EP1277826A1 (en) * | 2001-07-18 | 2003-01-22 | ATOFINA Research | Hydrogenation and dehydrogenation processes and catalysts therefor |
| DE102004007498A1 (de) * | 2004-02-13 | 2005-09-01 | Basf Ag | Hydrierverfahren zur Herstellung optisch aktiver Alkohole oder Carbonsäuren |
| KR100922998B1 (ko) * | 2008-03-06 | 2009-10-22 | 한국화학연구원 | 모노카르복실산 또는 그의 유도체로부터 일가 알콜의 제조방법 |
-
2010
- 2010-10-26 CN CN201080006216.9A patent/CN102300635B/zh not_active Expired - Fee Related
- 2010-10-26 RU RU2012121807/04A patent/RU2549893C2/ru not_active IP Right Cessation
- 2010-10-26 WO PCT/US2010/054134 patent/WO2011056595A1/en not_active Ceased
- 2010-10-26 BR BR112012009770A patent/BR112012009770A2/pt not_active Application Discontinuation
- 2010-10-26 EP EP10773794A patent/EP2493609A1/en not_active Withdrawn
- 2010-10-26 JP JP2012535457A patent/JP5775087B2/ja not_active Expired - Fee Related
- 2010-10-26 CA CA2778957A patent/CA2778957A1/en not_active Abandoned
- 2010-10-26 AU AU2010315552A patent/AU2010315552B2/en not_active Expired - Fee Related
- 2010-10-26 MX MX2012004841A patent/MX2012004841A/es unknown
-
2012
- 2012-04-18 ZA ZA2012/02847A patent/ZA201202847B/en unknown
- 2012-04-24 IL IL219400A patent/IL219400A0/en unknown
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