JP4783146B2 - プロピレンの少なくとも１種の部分酸化‐及び／又はアンモ酸化生成物の製法 - Google Patents
プロピレンの少なくとも１種の部分酸化‐及び／又はアンモ酸化生成物の製法 Download PDFInfo
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- JP4783146B2 JP4783146B2 JP2005500026A JP2005500026A JP4783146B2 JP 4783146 B2 JP4783146 B2 JP 4783146B2 JP 2005500026 A JP2005500026 A JP 2005500026A JP 2005500026 A JP2005500026 A JP 2005500026A JP 4783146 B2 JP4783146 B2 JP 4783146B2
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- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C7/04—Purification; Separation; Use of additives by distillation
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- C07C253/00—Preparation of carboxylic acid nitriles
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
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- C07C5/48—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with oxygen as an acceptor
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- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
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- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
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- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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- 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
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/88—Molybdenum
- B01J23/887—Molybdenum containing in addition other metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
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| DE10245585.6 | 2002-09-27 | ||
| DE10245585A DE10245585A1 (de) | 2002-09-27 | 2002-09-27 | Verfahren zur Herstellung von wenigstens einem partiellen Oxidations- und/oder Ammoxidationsprodukt des Propylens |
| DE10246119.8 | 2002-10-01 | ||
| DE2002146119 DE10246119A1 (de) | 2002-10-01 | 2002-10-01 | Verfahren zur Herstellung von wenigstens einem partiellen Oxidations- und/oder Ammoxidationsprodukt des Propylens |
| PCT/EP2003/010375 WO2004031107A1 (de) | 2002-09-27 | 2003-09-18 | Verfahren zur herstellung von wenigstens einem partiellen oxidations- und/oder ammoxidationsprodukt des propylens |
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Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7238827B2 (en) * | 2002-09-27 | 2007-07-03 | Basf Aktiengesellschaft | Preparation of at least one partial oxidation and/or ammoxidation product of propylene |
| US7253310B2 (en) * | 2003-08-19 | 2007-08-07 | Basf Aktiengesellschaft | Preparation of (meth)acrylic acid |
| US7019169B2 (en) * | 2003-09-23 | 2006-03-28 | Basf Aktiengesellschaft | Preparation of (meth)acrylic acid |
| US7012157B2 (en) | 2003-09-23 | 2006-03-14 | Basf Aktiengesellschaft | Preparation of (meth)acrylic acid |
| DE102004021764A1 (de) * | 2004-04-30 | 2005-06-02 | Basf Ag | Verfahren zur Herstellung von Acrylsäure durch heterogen katalysierte Gasphasenpartialoxidation wenigstens einer C3-Kohlenwasserstoffvorläuferverbindung |
| RU2391330C9 (ru) * | 2004-07-01 | 2011-05-10 | Басф Акциенгезельшафт | Способ получения акролеина, или акриловой кислоты, или их смеси из пропана |
| KR101206583B1 (ko) * | 2004-07-01 | 2012-11-29 | 바스프 에스이 | 프로필렌의 불균질 촉매화 부분 기상 산화에 의한아크릴산의 제조 방법 |
| US7592483B2 (en) * | 2004-07-01 | 2009-09-22 | Basf Aktiengesellschaft | Preparation of acrolein or acrylic acid or a mixture thereof by heterogeneously catalyzed partial gas phase oxidation of propylene |
| EP1765753B1 (de) * | 2004-07-01 | 2016-10-05 | Basf Se | Verfahren zur herstellung von acrolein oder acrylsäure oder deren gemisch durch heterogen katalysierte partielle gasphasenoxidation von propylen |
| JP5192827B2 (ja) * | 2005-03-01 | 2013-05-08 | ビーエーエスエフ ソシエタス・ヨーロピア | 主成分並びに目的生成物としてのアクリル酸及び副成分としてのメタクリル酸を含有する液相からのメタクリル酸の分離方法 |
| US7601866B2 (en) | 2005-03-01 | 2009-10-13 | Basf Aktiengesellschaft | Process for removing methacrolein from liquid phase comprising acrylic acid as a main constituent and target product, and methacrolein as a secondary component |
| US7705181B2 (en) * | 2005-03-01 | 2010-04-27 | Basf Akiengesellschaft | Process for removing methacrylic acid from liquid phase comprising acrylic acid as a main constituent and target product, and methacrylic acid as a secondary component |
| DE102005010586A1 (de) * | 2005-03-08 | 2006-09-14 | Basf Ag | Verfahren zur Herstellung von Propen aus Propan |
| DE102005019911A1 (de) * | 2005-04-27 | 2006-11-02 | Basf Ag | Verfahren der rektifikativen Auftrennung einer Acrylsäure und/oder Methacrylsäure enthaltenden Flüssigkeit |
| JP5231996B2 (ja) * | 2005-05-12 | 2013-07-10 | ビーエーエスエフ ソシエタス・ヨーロピア | プロピレンの部分酸化および／またはアンモ酸化による少なくとも１つの最終生成物の製造方法 |
| DE102005022798A1 (de) * | 2005-05-12 | 2006-11-16 | Basf Ag | Verfahren zur Herstellung wenigstens eines Zielproduktes durch partielle Oxidation und/oder Ammoxidation von Propylen |
| DE102005038412A1 (de) * | 2005-08-12 | 2007-02-15 | Basf Ag | Verfahren zur Deckung des Bedarfs an Polymerisaten I, die zu wenigstens 90% ihres Gewichtes Acrylsäure, deren Salze und/oder Alkylester der Acrylsäure radikalisch einpolymerisiert enthalten |
| US7388106B2 (en) * | 2005-10-14 | 2008-06-17 | Basf Aktiengesellschaft | Process for preparing acrolein or acrylic acid or a mixture thereof from propane |
| DE102005052923A1 (de) * | 2005-11-03 | 2007-05-10 | Basf Ag | Verfahren zum stabilen Betreiben eines kontinuierlich ausgeübten Herstellprozesses zur Erzeugung von Acrolein, oder Acrylsäure oder deren Gemisch aus Propan |
| KR101278795B1 (ko) * | 2005-11-03 | 2013-06-25 | 바스프 에스이 | 프로판으로부터 아크롤레인 또는 아크릴산 또는 그의혼합물을 수득하기 위한 안정한 연속 제조 방법 |
| RU2430083C9 (ru) * | 2005-11-24 | 2012-09-20 | Басф Се | Способ получения акриловой кислоты из пропана |
| KR101370749B1 (ko) * | 2005-11-24 | 2014-03-06 | 바스프 에스이 | 프로판으로부터 아크롤레인 또는 아크릴산, 또는 그의혼합물의 제조 방법 |
| DE102005061626A1 (de) * | 2005-12-21 | 2007-06-28 | Basf Ag | Verfahren der kontinuierlichen heterogen katalysierten partiellen Dehydrierung wenigstens eines zu dehydrierenden Kohlenwasserstoffs |
| DE102005062010A1 (de) | 2005-12-22 | 2007-06-28 | Basf Ag | Verfahren der heterogen katalysierten partiellen Gasphasenoxidation von Propylen zu Acrylsäure |
| DE102005062026A1 (de) * | 2005-12-22 | 2007-06-28 | Basf Ag | Verfahren der heterogen katalysierten partiellen Gasphasenoxidation von Propylen zu Acrylsäure |
| EP1734030A1 (de) * | 2006-01-18 | 2006-12-20 | BASF Aktiengesellschaft | Verfahren zum Langzeitbetrieb einer heterogen katalysierten partiellen Gasphasenoxidation einer organischen Ausgangsverbindung |
| EP1997554A4 (en) * | 2006-03-20 | 2011-02-23 | Asahi Kasei Chemicals Corp | OXIDATION- BZW. AMMOXIDATION CATALYST AND METHOD FOR THE PRODUCTION THEREOF |
| DE102006024901A1 (de) * | 2006-05-24 | 2007-11-29 | Basf Ag | Verfahren zur Herstellung von Acrolein, oder Acrylsäure oder deren Gemisch aus Propan |
| DE102006029790A1 (de) * | 2006-06-27 | 2008-01-03 | Basf Ag | Verfahren der kontinuierlichen heterogen katalysierten partiellen Dehydrierung wenigstens eines zu dehydrierenden Kohlenwasserstoffs |
| DE102006049939A1 (de) * | 2006-10-19 | 2008-04-24 | Basf Ag | Verfahren zur Trennung von in einem Produktgasgemisch einer partiellen heterogen katalysierten Gasphasenoxidation einer C3-Vorläuferverbindung der Acrylsäure enthaltener Acrylsäure und Benzoesäure |
| WO2008058918A1 (de) * | 2006-11-15 | 2008-05-22 | Basf Se | Verfahren zum betreiben einer exothermen heterogen katalysierten partiellen gasphasenoxidation einer organischen ausgangsverbindung zu einer organischen zielverbindung |
| DE102007006647A1 (de) * | 2007-02-06 | 2008-08-07 | Basf Se | Verfahren zur Regenerierung eines im Rahmen einer heterogen katalysierten partiellen Dehydrierung eines Kohlenwasserstoffs deaktivierten Katalysatorbetts |
| US8969644B2 (en) * | 2007-02-06 | 2015-03-03 | Basf Se | Method for providing an oxygen-containing gas stream for the endothermic reaction of an initial stream comprising one or more hydrocarbons |
| DE102007029053A1 (de) * | 2007-06-21 | 2008-01-03 | Basf Ag | Verfahren der heterogen katalysierten partiellen Direktoxidation von n-Propan zu Acrylsäure |
| JP5239997B2 (ja) * | 2008-03-31 | 2013-07-17 | 三菱化学株式会社 | プレート式反応器における温度制御方法及び反応生成物の製造方法 |
| DE102008044946B4 (de) * | 2008-08-29 | 2022-06-15 | Evonik Superabsorber Gmbh | Einsatz von Schaumkörpern in Oxidations-Reaktoren zur Herstellung ungesättigter Carbonsäuren |
| WO2012005835A1 (en) * | 2010-07-09 | 2012-01-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| WO2012005837A1 (en) * | 2010-07-09 | 2012-01-12 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| JP2013506001A (ja) * | 2010-07-10 | 2013-02-21 | 住友化学株式会社 | 酸化オレフィンの製造方法 |
| WO2012009056A1 (en) * | 2010-07-10 | 2012-01-19 | Sumitomo Chemical Company, Limited | Process for producing olefin oxide |
| JP2013505991A (ja) * | 2010-07-10 | 2013-02-21 | 住友化学株式会社 | 酸化オレフィンの製造方法 |
| DE102012212437A1 (de) | 2012-07-16 | 2014-01-16 | Basf Se | Verfahren zur Herstellung von Acrylsäure aus Ethylenoxid und Kohlenmonoxid |
| RU2668554C2 (ru) * | 2014-05-29 | 2018-10-02 | ИНЕОС Юроп АГ | Улучшенные селективные катализаторы аммоксидирования |
| US11111193B2 (en) | 2014-06-30 | 2021-09-07 | Shell Oil Company | Treatment of a mixed metal oxide catalyst containing molybdenum, vanadium, niobium and optionally tellurium |
| CA2953196A1 (en) * | 2014-06-30 | 2016-01-07 | Shell Internationale Research Maatschappij B.V. | Alkane oxidative dehydrogenation and/or alkene oxidation |
| CN106660901B (zh) * | 2014-06-30 | 2019-07-05 | 国际壳牌研究有限公司 | 烷烃氧化脱氢和/或烯烃氧化 |
| EP3026037A1 (en) * | 2014-11-26 | 2016-06-01 | Shell Internationale Research Maatschappij B.V. | Alkane oxidative dehydrogenation and/or alkene oxidation |
| CN108137465B (zh) | 2015-08-07 | 2021-06-01 | 巴斯夫欧洲公司 | 制备丙烯酸的方法 |
| RU2674664C1 (ru) * | 2015-09-25 | 2018-12-12 | Юоп Ллк | Способы и установки для производства бутадиена |
| KR20180100178A (ko) * | 2016-01-09 | 2018-09-07 | 어센드 퍼포먼스 머티리얼즈 오퍼레이션즈 엘엘씨 | 아크릴로나이트릴 반응기 공급 스트림에서 사이안화 수소의 직접 제조를 위한 촉매 조성물 및 공정 |
| US10160698B2 (en) * | 2016-10-28 | 2018-12-25 | Uop Llc | Use of membrane for oxidative-dehydrogenation process |
| US20220134312A1 (en) * | 2019-01-31 | 2022-05-05 | Basf Se | A molding comprising a mixed oxide comprising oxygen, lanthanum, aluminum, and cobalt |
| KR102519507B1 (ko) | 2019-09-30 | 2023-04-07 | 주식회사 엘지화학 | 프로필렌의 암모산화용 촉매, 이의 제조 방법, 및 이를 이용한 프로필렌의 암모산화 방법 |
| EP3974058B1 (en) | 2019-09-30 | 2024-10-30 | LG Chem, Ltd. | Catalyst for ammoxidation of propylene, method for preparing same, and method for ammoxidation of propylene using same |
| JP7174846B2 (ja) | 2019-09-30 | 2022-11-17 | エルジー・ケム・リミテッド | プロピレンのアンモ酸化用触媒、その製造方法、およびこれを利用したプロピレンのアンモ酸化方法 |
| WO2021153586A1 (ja) * | 2020-01-28 | 2021-08-05 | 東レ株式会社 | ｔｒａｎｓ，ｔｒａｎｓ－ムコン酸又はそのアルキルエステルの製造方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08245494A (ja) * | 1995-03-10 | 1996-09-24 | Basf Ag | プロパンからアクロレイン、アクリル酸又はこれらの混合物を製造する方法 |
| WO2001096271A2 (de) * | 2000-06-14 | 2001-12-20 | Basf Aktiengesellschaft | Verfahren zur herstellung von acrolein und/oder acrylsäure |
| WO2001096270A2 (de) * | 2000-06-14 | 2001-12-20 | Basf Aktiengesellschaft | Verfahren zur herstellung von acrolein oder acrylsäure oder deren gemisch aus propan |
| WO2002000587A1 (de) * | 2000-06-28 | 2002-01-03 | Basf Aktiengesellschaft | Verfahren zur herstellung von hydroformylierungsprodukten des propylens und von acrylsäure und/oder acrolein |
| WO2002006199A2 (de) * | 2000-07-18 | 2002-01-24 | Basf Aktiengesellschaft | Verfahren zur herstellung von acrylsäure durch heterogen katalysierte gasphasenoxidation von propan |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US482771A (en) * | 1892-09-20 | Thirds to frank a | ||
| US4658074A (en) * | 1965-05-28 | 1987-04-14 | Petro-Tex Chemical Corporation | Catalytic oxidative dehydrogenation process |
| BE759434A (fr) | 1969-11-25 | 1971-04-30 | Power Gas Ltd | Oxydation catalytique |
| CA939676A (en) * | 1970-03-24 | 1974-01-08 | David Naden | Catalytic oxidation |
| DE2251364B2 (de) * | 1971-10-22 | 1975-07-03 | Asahi Glass Co. Ltd., Tokio | Verfahren zur Herstellung von Acrylsäure bzw. Methacrylsäure aus Acrolein bzw. Methacrolein |
| US3798283A (en) * | 1972-03-08 | 1974-03-19 | Atlantic Richfield Co | Non-catalytic oxidative dehydrogenation process |
| US4077912A (en) * | 1972-10-12 | 1978-03-07 | Standard Oil Company | Catalysts useful for exothermic reactions |
| DE3461782D1 (en) * | 1983-02-22 | 1987-02-05 | Halcon Sd Group Inc | Conversion of propane to acrylic acid |
| NO163690C (no) | 1984-06-18 | 1990-07-04 | Air Prod & Chem | Fremgangsmaate for fremstilling av to kvaliteter av propylen. |
| AU606160B2 (en) | 1987-05-27 | 1991-01-31 | Nippon Shokubai Kagaku Kogyo Co. Ltd. | Process for production of acrylic acid |
| US5218146A (en) * | 1987-05-27 | 1993-06-08 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Process for production of acrylic acid |
| US5008414A (en) | 1988-12-08 | 1991-04-16 | The Boc Group, Inc. | Process for the production of oxides |
| US4943650A (en) * | 1989-01-30 | 1990-07-24 | The Boc Group, Inc. | Process for the production of nitriles |
| EP0529853B1 (en) | 1991-08-08 | 1996-02-28 | Mitsubishi Chemical Corporation | Catalyst and process for producing nitriles |
| FR2684989B1 (fr) * | 1991-12-16 | 1994-02-04 | Rhone Poulenc Chimie | Procede d'ammoxydation d'hydrocarbures satures. |
| US5268497A (en) * | 1992-02-24 | 1993-12-07 | The Boc Group, Inc. | Process for the production of nitriles |
| DE69402567T2 (de) | 1993-01-28 | 1997-11-27 | Mitsubishi Chem Corp | Methode zur Herstellung einer ungesättigten Carbonsäure |
| DE69505336T2 (de) * | 1994-11-14 | 1999-03-04 | Nippon Shokubai Co. Ltd., Osaka | Verfahren zur Herstellung von Acrylsäure |
| DE19530454A1 (de) | 1995-08-18 | 1997-02-20 | Manfred Prof Dr Baerns | Verfahren zur Gewinnung von Propen durch Umsetzung von Propan mit Sauerstoff an Katalysatoren |
| US6492548B1 (en) * | 1996-04-01 | 2002-12-10 | Union Carbide Chemicals & Plastics Technology Corporation | Process for the oxidation of alkanes |
| BR9708392A (pt) | 1996-04-01 | 1999-08-03 | Union Carbide Chem Plastic | Processo para oxidação de alcanos |
| US5973171A (en) | 1998-10-07 | 1999-10-26 | Arco Chemical Technology, Lp | Propylene oxide production |
| DE10051419A1 (de) | 2000-10-17 | 2002-04-18 | Basf Ag | Katalysator bestehend aus einem Trägerkörper und einer auf der Oberfläche des Trägerkörpers aufgebrachten katalytisch aktiven Oxidmasse |
| DE10119933A1 (de) | 2001-04-23 | 2002-10-24 | Basf Ag | Verfahren zur Herstellung von Acrylsäure durch heterogen katalysierte Gasphasenoxidation von Propan |
| DE10122027A1 (de) | 2001-05-07 | 2002-05-23 | Basf Ag | Verfahren zur Herstellung von Acrylsäure durch heterogen katalysierte Partialoxidation von Propan |
| JP3805178B2 (ja) * | 2000-07-31 | 2006-08-02 | 株式会社日本触媒 | メタクリル酸の回収方法 |
| DE10046928A1 (de) * | 2000-09-21 | 2002-04-11 | Basf Ag | Verfahren zur Herstellung von Multimetalloxidmassen |
| DE10046957A1 (de) * | 2000-09-21 | 2002-04-11 | Basf Ag | Verfahren zur Herstellung eines Multimetalloxid-Katalysators, Verfahren zur Herstellung ungesättigter Aldehyde und/oder Carbonsäuren und Bandcalziniervorrichtung |
| US6407280B1 (en) | 2000-09-28 | 2002-06-18 | Rohm And Haas Company | Promoted multi-metal oxide catalyst |
| DE10122029A1 (de) | 2001-05-07 | 2002-11-21 | Conti Temic Microelectronic | Beschleunigungsaufnehmer |
| DE10131297A1 (de) | 2001-06-29 | 2003-01-09 | Basf Ag | Verfahren zur Herstellung von partiellen Oxidationsprodukten und/oder partiellen Ammoxidationsprodukten wenigstens eines olefinischen Kohlenwasserstoffs |
| US7238827B2 (en) * | 2002-09-27 | 2007-07-03 | Basf Aktiengesellschaft | Preparation of at least one partial oxidation and/or ammoxidation product of propylene |
-
2003
- 2003-06-20 US US10/465,659 patent/US7238827B2/en not_active Expired - Lifetime
- 2003-06-20 US US10/465,656 patent/US7326802B2/en not_active Expired - Fee Related
- 2003-09-09 MY MYPI20033404A patent/MY132763A/en unknown
- 2003-09-18 BR BR0314772-0A patent/BR0314772A/pt not_active Application Discontinuation
- 2003-09-18 WO PCT/EP2003/010375 patent/WO2004031107A1/de not_active Ceased
- 2003-09-18 WO PCT/EP2003/010374 patent/WO2004031106A1/de not_active Ceased
- 2003-09-18 EP EP03769283.7A patent/EP1546073B1/de not_active Expired - Lifetime
- 2003-09-18 AU AU2003266395A patent/AU2003266395A1/en not_active Abandoned
- 2003-09-18 RU RU2005113156/04A patent/RU2346928C9/ru not_active IP Right Cessation
- 2003-09-18 AU AU2003277867A patent/AU2003277867A1/en not_active Abandoned
- 2003-09-18 JP JP2005500026A patent/JP4783146B2/ja not_active Expired - Fee Related
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- 2003-09-18 KR KR1020057005332A patent/KR100962755B1/ko not_active Expired - Fee Related
- 2003-09-18 RU RU2005113155/04A patent/RU2347772C2/ru not_active IP Right Cessation
- 2003-09-18 EP EP03798911.8A patent/EP1546074B1/de not_active Expired - Lifetime
- 2003-09-18 JP JP2005500025A patent/JP4588631B2/ja not_active Expired - Fee Related
- 2003-09-24 SA SA03240312A patent/SA03240312B1/ar unknown
- 2003-09-24 SA SA03240311A patent/SA03240311B1/ar unknown
-
2005
- 2005-04-26 ZA ZA2005/03357A patent/ZA200503357B/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08245494A (ja) * | 1995-03-10 | 1996-09-24 | Basf Ag | プロパンからアクロレイン、アクリル酸又はこれらの混合物を製造する方法 |
| WO2001096271A2 (de) * | 2000-06-14 | 2001-12-20 | Basf Aktiengesellschaft | Verfahren zur herstellung von acrolein und/oder acrylsäure |
| WO2001096270A2 (de) * | 2000-06-14 | 2001-12-20 | Basf Aktiengesellschaft | Verfahren zur herstellung von acrolein oder acrylsäure oder deren gemisch aus propan |
| WO2002000587A1 (de) * | 2000-06-28 | 2002-01-03 | Basf Aktiengesellschaft | Verfahren zur herstellung von hydroformylierungsprodukten des propylens und von acrylsäure und/oder acrolein |
| WO2002006199A2 (de) * | 2000-07-18 | 2002-01-24 | Basf Aktiengesellschaft | Verfahren zur herstellung von acrylsäure durch heterogen katalysierte gasphasenoxidation von propan |
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