JP2011529494A5 - - Google Patents
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- JP2011529494A5 JP2011529494A5 JP2011521093A JP2011521093A JP2011529494A5 JP 2011529494 A5 JP2011529494 A5 JP 2011529494A5 JP 2011521093 A JP2011521093 A JP 2011521093A JP 2011521093 A JP2011521093 A JP 2011521093A JP 2011529494 A5 JP2011529494 A5 JP 2011529494A5
- Authority
- JP
- Japan
- Prior art keywords
- acetic acid
- process according
- acetaldehyde
- selectivity
- palladium
- 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.)
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 21
- IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 8
- 238000000034 method Methods 0.000 claims 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 3
- 239000010949 copper Substances 0.000 claims 3
- 239000010931 gold Substances 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- 239000000377 silicon dioxide Substances 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 2
- 229910052737 gold Inorganic materials 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 2
- 239000012159 carrier gas Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
Claims (9)
- 酢酸及び水素を含む供給流を、２５０℃〜３５０℃の範囲の温度において、
（ａ）シリカ及び炭素からなる群から選択される触媒担体上の、０．５〜１．０重量％のパラジウムを含む第１の金属、並びに鉄、銅、金、カリウム、及びこれらの組み合わせからなる群から選択される第２の金属；
を含む水素化触媒と接触させることを含み、消費された酢酸を基準とするアセトアルデヒドへの選択率が少なくとも６０％である、酢酸からアセトアルデヒドを選択的且つ直接に生成する方法。 - 触媒担体がシリカである、請求項１に記載の方法。
- 消費された酢酸を基準とするアセトアルデヒドへの選択率が少なくとも７０％である、請求項１又は２に記載の方法。
- 消費された酢酸を基準とするアセトアルデヒドへの選択率が少なくとも８０％である、請求項１〜３のいずれか１項に記載の方法。
- アセトアルデヒドへの水素化を気相中で行う、請求項１〜４のいずれか１項に記載の方法。
- 供給流が不活性キャリアガスを含む、請求項１〜５のいずれか１項に記載の方法。
- 反応物質が１００：１〜１：１００の範囲のモル比の酢酸及び水素から構成される、請求項１〜６のいずれか１項に記載の方法。
- 反応物質が１：２０〜１：２の範囲のモル比の酢酸及び水素から構成される、請求項１〜７のいずれか１項記載の方法。
- 水素化触媒が、シリカ又は炭素上に担持されているパラジウム／金（Ｐｄ／Ａｕ）又はパラジウム／銅（Ｐｄ／Ｃｕ）の２元金属の組み合わせから選択される、請求項１〜８のいずれか１項に記載の方法。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
| US12/221,135 | 2008-07-31 | ||
| PCT/US2009/004187 WO2010014146A2 (en) | 2008-07-31 | 2009-07-20 | Direct and selective production of acetaldehyde from acetic acid utilizing a supported metal catalyst |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012051874A Division JP5108980B2 (ja) | 2008-07-31 | 2012-03-08 | 担持金属触媒を用いる酢酸からのアセトアルデヒドの直接及び選択的な製造 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011529494A JP2011529494A (ja) | 2011-12-08 |
| JP2011529494A5 true JP2011529494A5 (ja) | 2012-06-21 |
| JP5053458B2 JP5053458B2 (ja) | 2012-10-17 |
Family
ID=41354062
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011521093A Expired - Fee Related JP5053458B2 (ja) | 2008-07-31 | 2009-07-20 | 担持金属触媒を用いる酢酸からのアセトアルデヒドの直接及び選択的な製造 |
| JP2012051874A Expired - Fee Related JP5108980B2 (ja) | 2008-07-31 | 2012-03-08 | 担持金属触媒を用いる酢酸からのアセトアルデヒドの直接及び選択的な製造 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012051874A Expired - Fee Related JP5108980B2 (ja) | 2008-07-31 | 2012-03-08 | 担持金属触媒を用いる酢酸からのアセトアルデヒドの直接及び選択的な製造 |
Country Status (14)
| Country | Link |
|---|---|
| US (4) | US7816565B2 (ja) |
| EP (1) | EP2318348A2 (ja) |
| JP (2) | JP5053458B2 (ja) |
| KR (1) | KR20110047209A (ja) |
| CN (1) | CN102143932A (ja) |
| AR (1) | AR074714A1 (ja) |
| AU (1) | AU2009277184B2 (ja) |
| CA (1) | CA2732364A1 (ja) |
| CO (1) | CO6541516A2 (ja) |
| IL (1) | IL210947A0 (ja) |
| RU (1) | RU2011107273A (ja) |
| TW (1) | TW201012785A (ja) |
| WO (1) | WO2010014146A2 (ja) |
| ZA (1) | ZA201100790B (ja) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8501652B2 (en) * | 2008-07-31 | 2013-08-06 | Celanese International Corporation | Catalysts 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 |
| 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 |
| 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 |
| 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 |
| US8637714B2 (en) | 2008-07-31 | 2014-01-28 | Celanese International Corporation | Process for producing ethanol over catalysts containing platinum and palladium |
| US8546622B2 (en) | 2008-07-31 | 2013-10-01 | Celanese International Corporation | Process for making ethanol from acetic acid using acidic catalysts |
| 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 |
| US8222466B2 (en) | 2010-02-02 | 2012-07-17 | Celanese International Corporation | Process for producing a water stream from ethanol production |
| US8460405B2 (en) | 2010-02-02 | 2013-06-11 | Celanese International Corporation | Ethanol compositions |
| US8575403B2 (en) | 2010-05-07 | 2013-11-05 | Celanese International Corporation | Hydrolysis of ethyl acetate in ethanol separation process |
| EP2531292A2 (en) | 2010-02-02 | 2012-12-12 | 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 |
| US8932372B2 (en) | 2010-02-02 | 2015-01-13 | Celanese International Corporation | Integrated process for producing alcohols from a mixed acid feed |
| 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 |
| US8747492B2 (en) | 2010-02-02 | 2014-06-10 | Celanese International Corporation | Ethanol/fuel blends for use as motor fuels |
| 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 |
| US8344186B2 (en) | 2010-02-02 | 2013-01-01 | Celanese International Corporation | Processes for producing ethanol from acetaldehyde |
| 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 |
| 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 |
| US9272970B2 (en) | 2010-07-09 | 2016-03-01 | Celanese International Corporation | Hydrogenolysis of ethyl acetate in alcohol separation processes |
| WO2012148509A1 (en) | 2011-04-26 | 2012-11-01 | Celanese International Corporation | Process for producing ethanol using a stacked bed reactor |
| 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 |
| US9073816B2 (en) | 2011-04-26 | 2015-07-07 | Celanese International Corporation | Reducing ethyl acetate concentration in recycle streams for ethanol production processes |
| 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 |
| US8592635B2 (en) | 2011-04-26 | 2013-11-26 | Celanese International Corporation | Integrated ethanol production by extracting halides from acetic acid |
| US8754268B2 (en) | 2011-04-26 | 2014-06-17 | Celanese International Corporation | Process for removing water from alcohol mixtures |
| US8895786B2 (en) | 2011-08-03 | 2014-11-25 | Celanese International Corporation | Processes for increasing alcohol production |
| US8853466B2 (en) | 2011-08-19 | 2014-10-07 | Celanese International Corporation | Integrated process for producing ethanol from methanol |
| US8829253B2 (en) | 2011-08-19 | 2014-09-09 | 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 |
| DE102013106790A1 (de) | 2013-06-28 | 2014-12-31 | Oxea Gmbh | Verfahren zur Herstellung von 1,3-Butandiol |
| DE102013106787A1 (de) | 2013-06-28 | 2014-12-31 | Oxea Gmbh | Verfahren zur Herstellung von n-Butanderivaten |
| WO2015156061A1 (ja) * | 2014-04-10 | 2015-10-15 | 株式会社ダイセル | アセトアルデヒドの製造方法 |
| WO2015163020A1 (ja) * | 2014-04-22 | 2015-10-29 | 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 |
| JP6723151B2 (ja) * | 2014-04-28 | 2020-07-15 | 株式会社ダイセル | 酢酸とアセトアルデヒドと酢酸エチルの製造方法 |
| 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 |
Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2105540A (en) | 1935-01-09 | 1938-01-18 | Du Pont | Catalytic hydrogenation process for the production of aldehydes |
| US2882244A (en) | 1953-12-24 | 1959-04-14 | Union Carbide Corp | Molecular sieve adsorbents |
| US3130007A (en) | 1961-05-12 | 1964-04-21 | Union Carbide Corp | Crystalline zeolite y |
| GB1168785A (en) | 1965-09-24 | 1969-10-29 | British Petroleum Co | Graphite |
| US3702886A (en) | 1969-10-10 | 1972-11-14 | Mobil Oil Corp | Crystalline zeolite zsm-5 and method of preparing the same |
| US4018514A (en) | 1975-09-25 | 1977-04-19 | Polaroid Corporation | Apparatus for retinal photography |
| US4328373A (en) | 1980-03-17 | 1982-05-04 | The Dow Chemical Company | Method of preparing aldehydes |
| CA1226585A (en) * | 1980-05-19 | 1987-09-08 | Masuhiko Tamura | Process for producing acetaldehyde |
| US4398039A (en) | 1981-05-18 | 1983-08-09 | The Standard Oil Company | Hydrogenation of carboxylic acids |
| US4443639A (en) | 1981-05-18 | 1984-04-17 | The Standard Oil Company (Indiana) | Hydrogenation of carboxylic acids |
| US4421939A (en) | 1982-10-15 | 1983-12-20 | Union Carbide Corporation | Production of ethanol from acetic acid |
| US4480115A (en) | 1983-03-17 | 1984-10-30 | Celanese Corporation | Direct hydrogenation of carboxylic acids to alcohol and esters |
| GB8307612D0 (en) | 1983-03-18 | 1983-04-27 | British Petroleum Co Plc | Ammonia production and catalysts |
| US4550185A (en) | 1983-12-22 | 1985-10-29 | E. I. Du Pont De Nemours And Company | Process for making tetrahydrofuran and 1,4-butanediol using Pd/Re hydrogenation catalyst |
| DE3562619D1 (en) | 1984-01-18 | 1988-06-16 | Mitsubishi Chem Ind | Catalytic process of producing aromatic aldehydes |
| 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 |
| GB8828616D0 (en) | 1988-12-07 | 1989-01-11 | Bp Chem Int Ltd | Chemical process |
| DE3927786A1 (de) * | 1989-08-23 | 1991-02-28 | Bayer Ag | Verfahren zur herstellung von aldehyden |
| US5008235A (en) | 1989-12-21 | 1991-04-16 | Union Carbide Chemicals And Plastics Technology Corporation | Catalysts of Cu-Al-third metal for hydrogenation |
| US5137861A (en) | 1991-01-22 | 1992-08-11 | Mobil Oil Corp. | Catalyst comprising a hydrogenation metal and a delaminated layered silicate |
| FR2682949B1 (fr) * | 1991-10-24 | 1993-12-17 | Rhone Poulenc Chimie | Procede de synthese d'aldehydes. |
| US5243095A (en) | 1992-04-24 | 1993-09-07 | Engelhard Corporation | Hydrogenation catalyst, process for preparing and process for using said catalyst |
| JP3295960B2 (ja) | 1992-05-12 | 2002-06-24 | 三菱化学株式会社 | アルデヒド類の製造方法 |
| JPH06116182A (ja) | 1992-10-09 | 1994-04-26 | Mitsubishi Kasei Corp | 有機カルボン酸及び／又は有機カルボン酸エステルの水素化方法 |
| US5821111A (en) | 1994-03-31 | 1998-10-13 | Bioengineering Resources, Inc. | Bioconversion of waste biomass to useful products |
| US5350504A (en) | 1992-12-18 | 1994-09-27 | Mobil Oil Corporation | Shape selective hydrogenation of aromatics over modified non-acidic platinum/ZSM-5 catalysts |
| USRE35377E (en) | 1993-05-27 | 1996-11-12 | Steinberg; Meyer | Process and apparatus for the production of methanol from condensed carbonaceous material |
| US5977010A (en) | 1995-06-15 | 1999-11-02 | Engelhard Corporation | Shaped hydrogenation catalyst and processes for their preparation and use |
| FR2740707B1 (fr) | 1995-11-08 | 1997-12-26 | Rhone Poulenc Chimie | Procede de preparation d'un catalyseur bi-metallique ruthenium/etain |
| 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 |
| US6121498A (en) * | 1998-04-30 | 2000-09-19 | Eastman Chemical Company | Method for producing acetaldehyde from acetic acid |
| US6294703B1 (en) | 1998-06-22 | 2001-09-25 | Mitsubishi Chemical Company | Process for the manufacture of cycloalkyldimethanol |
| EP0990638A1 (en) | 1998-10-01 | 2000-04-05 | Kvaerner Process Technology Limited | Process |
| US5945570A (en) | 1998-10-29 | 1999-08-31 | Arhancet; Juan Pedro | Catalyst and process for preparing 1,3-propanediol |
| DE19942895A1 (de) | 1999-09-08 | 2001-03-15 | Basf Ag | Katalysator und Verfahren zur Hydrierung von Carbonylverbindungen |
| US6495730B1 (en) | 1999-09-21 | 2002-12-17 | Asahi Kasei Kabushiki Kaisha | Catalysts for hydrogenation of carboxylic acid |
| US6232352B1 (en) | 1999-11-01 | 2001-05-15 | Acetex Limited | Methanol plant retrofit for acetic acid manufacture |
| AU2002240870A1 (en) | 2000-12-23 | 2002-07-08 | Degussa Ag | Method for producing alcohols by hydrogenating carbonyl compounds |
| 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 |
| JP3786007B2 (ja) | 2001-05-29 | 2006-06-14 | 住友金属鉱山株式会社 | 炭化水素油中に含む芳香族化合物の水素化処理用触媒 |
| EP1277826A1 (en) | 2001-07-18 | 2003-01-22 | ATOFINA Research | Hydrogenation and dehydrogenation processes and catalysts therefor |
| JP2007534477A (ja) | 2004-04-26 | 2007-11-29 | ハーテーエー・アクチェンゲゼルシャフト・ザ・ハイ・スループット・イクスペリメンテイション・カンパニー | 酸素リッチな排ガスから一酸化炭素および炭化水素を同時除去するための触媒、ならびにその製造方法 |
| WO2007117590A2 (en) | 2006-04-05 | 2007-10-18 | Woodland Biofuels Inc. | System and method for converting biomass to ethanol via syngas |
| US7538060B2 (en) | 2007-02-14 | 2009-05-26 | Eastman Chemical Company | Palladium-copper chromite hydrogenation catalysts |
| US7425657B1 (en) | 2007-06-06 | 2008-09-16 | Battelle Memorial Institute | Palladium catalyzed hydrogenation of bio-oils and organic compounds |
| US8502001B2 (en) | 2007-11-14 | 2013-08-06 | Bp P.L.C. | Process for the production of alcohol from a carbonaceous feedstock |
| EA016551B1 (ru) | 2007-11-14 | 2012-05-30 | Бп П.Л.К. | Способ получения спирта из углеродсодержащего сырья |
| WO2009086839A2 (en) | 2008-01-07 | 2009-07-16 | Danmarks Tekniske Universitet - Dtu | A catalyst, a process for selective hydrogenation of acetylene to ethylene and a method for the manufacture of the catalyst |
| US20090221725A1 (en) | 2008-02-28 | 2009-09-03 | Enerkem, Inc. | Production of ethanol from methanol |
| US8080693B2 (en) | 2008-02-28 | 2011-12-20 | Enerkem, Inc. | Production of ethanol from methanol |
| 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 |
| 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 |
| US7608744B1 (en) | 2008-07-31 | 2009-10-27 | Celanese International Corporation | Ethanol production from acetic acid utilizing a cobalt catalyst |
| US7820852B2 (en) | 2008-07-31 | 2010-10-26 | Celanese International Corporation | Direct and selective production of ethyl acetate from acetic acid utilizing a bimetal supported catalyst |
| US7884253B2 (en) | 2008-12-11 | 2011-02-08 | Range Fuels, Inc. | Methods and apparatus for selectively producing ethanol from synthesis gas |
| US8178715B2 (en) | 2008-12-31 | 2012-05-15 | Celanese International Corporation | Integrated process for the production of vinyl acetate from acetic acid via acetaldehyde |
-
2008
- 2008-07-31 US US12/221,135 patent/US7816565B2/en not_active Expired - Fee Related
-
2009
- 2009-07-20 CA CA2732364A patent/CA2732364A1/en not_active Abandoned
- 2009-07-20 CN CN2009801340830A patent/CN102143932A/zh active Pending
- 2009-07-20 WO PCT/US2009/004187 patent/WO2010014146A2/en active Application Filing
- 2009-07-20 EP EP09788947A patent/EP2318348A2/en 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 RU RU2011107273/04A patent/RU2011107273A/ru not_active Application Discontinuation
- 2009-07-20 KR KR1020117004664A patent/KR20110047209A/ko not_active Application Discontinuation
- 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
-
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
-
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
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