JP5764292B2 - 脱水素化される炭化水素の連続実施型不均一系触媒部分脱水素化の長期実施方法 - Google Patents
脱水素化される炭化水素の連続実施型不均一系触媒部分脱水素化の長期実施方法 Download PDFInfo
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- JP5764292B2 JP5764292B2 JP2009522207A JP2009522207A JP5764292B2 JP 5764292 B2 JP5764292 B2 JP 5764292B2 JP 2009522207 A JP2009522207 A JP 2009522207A JP 2009522207 A JP2009522207 A JP 2009522207A JP 5764292 B2 JP5764292 B2 JP 5764292B2
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- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
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Description
壁厚2mmおよび内径35mmおよび長さ80cmのEN材料番号1.4835の鋼鉄製反応チューブを以下のように充填する:
適切な脱水素化触媒の床50mlを反応チューブの中央に置く。成形触媒体の床上下で反応チューブを各場合、球径1.5〜2.5mmを有するステアタイト球(不活性球)の床で充填する。グリッドは床全体を担持する。外側から、反応チューブをその長さ全体にわたり550℃に維持する。反応チューブに、1000Nl/l・hの成形触媒体の床を負荷するプロパンを用いて体積比が2(プロパン)対1(蒸気)のプロパンと蒸気の混合物を入れる。反応チューブに入れた反応ガス混合物流を550℃に予熱する。本発明における方法において、上記の境界条件下において、エタン、エチレンおよびメタン副生成物の形成の累積的選択性が、変換したプロパンに対して≦5mol%である脱水素化触媒が特に好ましい。
単純な方法において、本発明の目的を、例えば、本発明における方法の全触媒床を反応ガス混合物流の流動方向において全固定触媒床に存在する脱水素化触媒の合計量Mの3区分の1つ目内および流動方向においてこの量Mの3区分の2つ目および最後内でともに断熱的に構成することにより実現することができるが、特定の断熱的3区分に入る前に反応ガス混合物の熱量を変化させることも可能である。
はじめに、反応帯域RZから回収された生成ガス流を、脱水素化炭化水素(例えば、プロピレン)および(未変換の)脱水素化される炭化水素(例えば、プロパン)以外のその構成物質(例えば、H2、H2O、N2など)の少なくとも1部分をそのまま、または除去後のような場合に使用して、少なくとも1つの酸化リアクターに入れ、充填ガス混合物に存在する脱水素化炭化水素(例えば、プロピレン)は、分子酸素を用いた選択的不均一系触媒部分気相酸化を行い、(部分酸化生成物である)標的生成物(例えば、アクロレインまたはアクリル酸あるいはその混合物)を含む部分酸化生成ガス混合物、さらに一般に脱水素化される未変換の炭化水素(例えば、プロパン)、過剰の分子酸素および適切であれば、未変換の脱水素化炭化水素(例えば、プロピレン)を得る。
≧0〜20または〜10、たびたび0〜6体積%のプロピレン、
≧0〜1、多くの場合0〜0.5、たびたび0〜0.25体積%、好ましくは0〜0.05体積%のアクロレイン、
≧0〜0.25(または〜0.4)、多くの場合0〜0.05、たびたび0〜0.03体積%のアクリル酸、
≧0〜20または〜5、多くの場合0〜3、たびたび0〜2体積%のCOx、
5〜50、好ましくは20〜40体積%のプロパン、
20または30〜80、好ましくは50〜70体積%の窒素、
≧0〜5、好ましくは1.0〜2.0体積%の酸素、
≧0〜20、好ましくは5.0〜10.0体積%のH2Oおよび
≧0、たびたび≧0.01、しばしば≧0.05〜10、好ましくは1〜5体積%のH2
を含むことができる。
a)N2およびH2O、
b)N2、O2およびH2O、
c)N2、O2、H2OおよびH2、
d)N2、O2、H2O、H2およびCO2、
e)N2、O2、H2O、H2、CO2およびCO
を含むことができる。
全触媒床に新しい脱水素化触媒を入れた。全固定触媒床に供給された反応ガス混合物流は、粗製プロパン、蒸気とアクリル酸への脱水素化で得られたプロピレンの不均一系触媒による2段階部分酸化の部分酸化循環ガスの混合物であった。プロパンおよびプロピレン以外の構成物質を独国出願第102005013039号の比較実施例1に記載のように、吸収/脱離手段(空気を用いた揮散)により脱水素化の生成ガス混合物から取り出した。プロピレンのアクリル酸への部分酸化を、同様に独国出願第102005013039号に記載のように行った。同じく、部分酸化循環ガスの形成に適用する。
A=12mol%、
B=5.4mol%、
C=1.8mol%および
G=19.2mol%
各場合、KWに対する。
実施時間の増加に伴う全固定触媒床の不活性を弱めるために、T1とMI(図1=M1)およびMII(図1=M2)はともに(上昇したデータ点により)図1に示されるように実施時間の増加に伴い次第に上昇した(左側縦軸=T1℃;右側縦軸=空気流量Nl/h;ゼロ点をt0に置いた;横座標はt時間を示す)。この方法において、0h=t0<t≦50hの実施時間間隔にわたり間隔G=19.2±0.2mol%内でG値を安定させることが可能であった。実施時間間隔の上昇した変換割合A、B、C(縦軸としてKWのmol%)の時間に対して得られた特性(横軸はt時間を示す)を、第2図に示す。
開始を、a)、b)に記載のものと同一の方法において行った。実施時間の増加に伴う全固定触媒床の不活性を弱めるために、T1と空気流量MIおよびMIIはそれぞれ、脱水素化変換に対する寄与A、B、Cおよびこれらとともに、これらの合計Gが安定したままであるように実施時間の増加に伴い上昇した。
上記の教示に関して、本発明に対する多数の修正および本発明からの逸脱は可能である。
それゆえ、添付された特許請求の範囲の範囲内で本発明を、具体的に本明細書に記載の方法と異なり実施できることを前提とできる。
Claims (32)
- 脱水素化される炭化水素の脱水素化炭化水素への連続実施型不均一系触媒部分脱水素化の長期実施の方法であって、前記脱水素化される炭化水素の不均一系触媒部分脱水素化のために、炭化水素をモル出発量KWで含む反応ガス混合物流を高温にて全触媒床に通して入れ、この触媒床は反応帯域RZに配置され、反応ガス混合物流の流動方向において連続して配列された複数の部分触媒床からなってよく、合計して脱水素化触媒の量Mを含み、こうして、実施時間t=t0時に、反応ガス混合物流が流動方向において量Mの3区分の1つ目を通過した場合に、脱水素化される炭化水素のモル出発量KWのAmol%の割合が脱水素化炭化水素に変換され、反応ガス混合物流が流動方向において量Mの3区分の2つ目を通過した場合に、脱水素化される炭化水素のモル出発量KWのBmol%の割合が脱水素化炭化水素に変換され、そして反応ガス混合物流が流動方向において量Mの3区分の最後を通過した場合に、脱水素化される炭化水素のモル出発量KWのCmol%の割合が脱水素化炭化水素に変換されるが、ただし、A>B>Cであり、かつ反応ガス混合物流が全触媒床を通過した場合に、合計G=前記混合物中に含まれる脱水素化される炭化水素のモル出発量KWの(A+B+C)mol%が脱水素化炭化水素に脱水素化され、その際、前記反応ガス混合物流に、全触媒床が始まるその入口と全触媒床が終わるその出口との間で、場合により、分子酸素、分子水素、水蒸気および/または他の不活性ガスの流量が、脱水素化補助ガスとして供給され、かつ実施時間の増加に伴いt0<t<tRの実施時間間隔[tRは、脱水素化が中断され、かつ全触媒床が実施時間t=t0後にはじめて再生される時の実施時間tである]において現れる全触媒床の不活性化を抑えるために、全触媒床内の反応ガス混合物流の温度推移および/または場合により供給される脱水素化補助ガスの流量の流量が変更される方法において、前記の変更を、前記実施時間tの増加に伴って、割合Aが減少し、割合Bが最大値を通過し、割合Cが増加するように実施することを特徴とする方法。
- 脱水素化される炭化水素がC2−〜C6−アルカンであり、脱水素化炭化水素がC2−〜C6−アルケンであることを特徴とする、請求項1に記載の方法。
- 脱水素化される炭化水素がn−プロパンであり、脱水素化炭化水素がプロピレンであることを特徴とする、請求項1に記載の方法。
- 脱水素化される炭化水素のモル出発量KWを含む反応ガス混合物流がさらに水蒸気を含むことを特徴とする、請求項1から3までのいずれか1項に記載の方法。
- 脱水素化される炭化水素のモル出発量KWを含む反応ガス混合物流がさらに分子酸素を含むことを特徴とする、請求項1から4までのいずれか1項に記載の方法。
- 脱水素化される炭化水素のモル出発量KWを含む反応ガス混合物流がさらに分子水素を含むことを特徴とする、請求項1から5までのいずれか1項に記載の方法。
- 実施時間t0時のGが10〜60mol%であることを特徴とする、請求項1から6までのいずれか1項に記載の方法。
- 実施時間t0時のGが15〜40mol%であることを特徴とする、請求項1から6までのいずれか1項に記載の方法。
- 実施時間t0時のGが15〜30mol%であることを特徴とする、請求項1から6までのいずれか1項に記載の方法。
- 全体の変換G=(A+B+C)に対して、実施時間t=t0時にて部分変換Aが45〜80%であり、部分変換Bが20〜40%であり、部分変換Cが0〜15%であることを特徴とする、請求項1から9までのいずれか1項に記載の方法。
- 全体の変換G=(A+B+C)に対して、実施時間t=t0時にて部分変換Aが55〜70%であり、部分変換Bが20〜35%であり、部分変換Cが7〜13%であることを特徴とする、請求項1から9までのいずれか1項に記載の方法。
- 実施時間の増加に伴いt0<t<tRの実施時間間隔において、部分変換Aが部分変換Cより低下するため、C>Aであることを特徴とする、請求項1から11までのいずれか1項に記載の方法。
- 実施時間の増加に伴いt0<t<tRの実施時間間隔において、部分変換A、B、Cの列がA>B>Cから始まり反転し、C>B>Aになることを特徴とする、請求項1から11までのいずれか1項に記載の方法。
- 前記A値がt0<t<tRの実施時間間隔において実施時間t=t0時のその値の20%を下回らないことを特徴とする、請求項1から13までのいずれか1項に記載の方法。
- 前記B、C値がt0<t<tRの実施時間間隔において実施時間t=t0時のA値の95%を上回らないことを特徴とする、請求項1から14までのいずれか1項に記載の方法。
- 反応帯域RZが断熱多段型リアクターとして構成され、同時に、段の間で分子酸素を含む脱水素化補助ガスの流量が供給されることを特徴とする、請求項1から15までのいずれか1項に記載の方法。
- 反応帯域RZが連続連結の少なくとも2つの断熱脱水素化リアクターとして設計され、同時に、直接的に連続連結された断熱脱水素化リアクター間で分子酸素を含む脱水素化補助ガスの流量が供給されることを特徴とする、請求項1から15までのいずれか1項に記載の方法。
- 全触媒床が固定床であることを特徴とする、請求項1から17までのいずれか1項に記載の方法。
- 脱水素化触媒が酸化物担体上に堆積した少なくとも1種の金属を有するものであることを特徴とする、請求項1から18までのいずれか1項に記載の方法。
- 少なくとも1種の金属が白金族からの元素であることを特徴とする、請求項19に記載の方法。
- 少なくとも1種の金属が白金であることを特徴とする、請求項19に記載の方法。
- 反応帯域RZで形成される脱水素化炭化水素および反応帯域RZで変換されない脱水素化される炭化水素を含む生成ガス流を反応帯域RZから取り出し、この生成ガス流を、そのままで、または脱水素化炭化水素および脱水素化される炭化水素とは異なるその構成物質の少なくとも部分量を取り出した後に使用して、少なくとも1つの酸化リアクターに入れ、前記リアクター内でその中に存在する脱水素化炭化水素を分子酸素を用いて選択的不均一系触媒部分気相酸化を行い、部分酸化生成物を含む部分酸化生成ガス混合物を得ることを特徴とする、請求項1から21までのいずれか1項に記載の方法。
- 脱水素化される炭化水素がプロパンであり、脱水素化炭化水素がプロピレンであり、部分酸化生成物がアクロレイン、アクリル酸またはその混合物であることを特徴とする、請求項22に記載の方法。
- 選択的不均一系触媒部分気相酸化の分離帯域において、引き続き部分酸化生成ガス混合物から部分酸化生成物を分離し、その際残留する未変換の脱水素化炭化水素、分子酸素ならびに場合により未変換の脱水素化炭化水素を含む残留ガスから、未変換の脱水素化される炭化水素を含有する少なくとも一部分量を、部分酸化循環ガスとして反応帯域RZへと再循環させることを特徴とする、請求項22に記載の方法。
- 部分酸化生成物を凝縮相への変換により分離帯域の部分酸化生成ガス混合物から分離することを特徴とする、請求項24に記載の方法。
- 部分酸化生成物がアクリル酸であり、凝縮相への変換が吸収および/または凝縮手段により行われることを特徴とする、請求項25に記載の方法。
- 凝縮相からのアクリル酸の分離が少なくとも1つの熱分離プロセスを使用して行われることを特徴とする、請求項26に記載の方法。
- 少なくとも1つの熱分離プロセスが液相からのアクリル酸の晶析分離を含むことを特徴とする、請求項27に記載の方法。
- 晶析分離が懸濁晶析であることを特徴とする、請求項28に記載の方法。
- アクリル酸の分離に引き続きラジカル重合のプロセスを行い、分離されたアクリル酸をラジカル的に重合導入して、ポリマーを製造することを特徴とする、請求項27に記載の方法。
- アクリル酸の分離に引き続きアクリル酸エステルを製造するプロセスを行い、分離されたアクリル酸をアルコールでエステル化することを特徴とする、請求項27に記載の方法。
- アクリル酸エステルを製造するプロセスに引き続きラジカル重合のプロセスを行い、こうして製造されたアクリル酸エステルを重合導入することを特徴とする、請求項31に記載の方法。
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US60/833,776 | 2006-07-28 | ||
PCT/EP2007/057407 WO2008012249A2 (de) | 2006-07-28 | 2007-07-18 | Verfahren zum langzeitbetrieb einer kontinuierlich betriebenen heterogen katalysierten partiellen dehydrierung eines zu dehydrierenden kohlenwasserstoffs |
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Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102006035718A1 (de) * | 2006-07-28 | 2008-01-31 | Basf Ag | Verfahren zum Langzeitbetrieb einer kontinuierlich betriebenen heterogen katalysierten partiellen Dehydrierung eines zu dehydrierenden Kohlenwasserstoffs |
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 |
EP2586524A1 (en) * | 2011-10-24 | 2013-05-01 | Borealis AG | A catalyst bed system for an endothermic catalytic dehydrogenation process and an endothermic dehydrogenation process |
JP6217442B2 (ja) * | 2013-03-29 | 2017-10-25 | 日本ゼオン株式会社 | イソプレンの製造方法 |
WO2015152159A1 (ja) * | 2014-03-31 | 2015-10-08 | 三井化学株式会社 | 不飽和炭化水素の製造方法 |
CN105017102B (zh) * | 2014-04-29 | 2017-03-01 | 中国石油化工股份有限公司 | 一种二甲基硫醚氧化方法 |
US20160090337A1 (en) * | 2014-09-30 | 2016-03-31 | Uop Llc | Paraffin dehydrogenation with oxidative reheat |
JP6527364B2 (ja) * | 2015-03-30 | 2019-06-05 | 三井化学株式会社 | ブタジエンを含む生成物の製造方法 |
CN114700005B (zh) * | 2022-06-06 | 2022-09-13 | 天津渤海石化有限公司 | Pdh工艺中反应器台数可变的自适应控制方法 |
Family Cites Families (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2452569A (en) * | 1946-09-10 | 1948-11-02 | Houdry Process Corp | Process of treating hydrocarbons in presence of hot contact masses |
BE789153A (fr) * | 1971-09-23 | 1973-03-22 | Aquitaine Petrole | Perfectionnement a la fabrication du styrene |
US4788371A (en) | 1987-12-30 | 1988-11-29 | Uop Inc. | Catalytic oxidative steam dehydrogenation process |
GB8807732D0 (en) * | 1988-03-31 | 1988-05-05 | Bp Chem Int Ltd | Hydrocarbon dehydrogenation reactions |
US4886928A (en) | 1988-09-26 | 1989-12-12 | Uop | Hydrocarbon dehydrogenation process |
US6740228B1 (en) * | 1989-10-30 | 2004-05-25 | Exxonmobil Chemical Patents Inc. | Process for reforming petroleum hydrocarbon stocks |
US5235121A (en) | 1991-08-02 | 1993-08-10 | Phillips Petroleum Company | Method for reforming hydrocarbons |
US5491275A (en) * | 1993-04-26 | 1996-02-13 | Uop | Process for the dehydrogenation of paraffinic hydrocarbons |
US5689029A (en) * | 1993-04-26 | 1997-11-18 | Uop | Process for the dehydrogenation of paraffinic hydrocarbons |
US5527979A (en) | 1993-08-27 | 1996-06-18 | Mobil Oil Corporation | Process for the catalytic dehydrogenation of alkanes to alkenes with simultaneous combustion of hydrogen |
US5430209A (en) | 1993-08-27 | 1995-07-04 | Mobil Oil Corp. | Process for the catalytic dehydrogenation of alkanes to alkenes with simultaneous combustion of hydrogen |
US5563314A (en) | 1993-08-27 | 1996-10-08 | Agaskar; Pradyot A. | Process for the catalytic dehydrogenation of alkanes to alkenes with simultaneous combustion of hydrogen |
US5530171A (en) | 1993-08-27 | 1996-06-25 | Mobil Oil Corporation | Process for the catalytic dehydrogenation of alkanes to alkenes with simultaneous combustion of hydrogen |
US5510557A (en) * | 1994-02-28 | 1996-04-23 | Abb Lummus Crest Inc. | Endothermic catalytic dehydrogenation process |
FI98529C (fi) * | 1994-03-31 | 1997-07-10 | Neste Oy | Menetelmä ja laitteisto keveiden olefiinien valmistamiseksi |
US5994606A (en) * | 1995-03-08 | 1999-11-30 | Mitsubishi Chemical Corporation | Method for dehydrogenation of hydrocarbon |
DE19833049A1 (de) * | 1998-07-22 | 2000-01-27 | Basf Ag | Verfahren zur Herstellung von Acrylsäure |
DE19937107A1 (de) | 1999-08-06 | 2001-02-08 | Basf Ag | Katalysator mit bimodaler Porenradienverteilung |
DE10028582A1 (de) * | 2000-06-14 | 2001-12-20 | Basf Ag | Verfahren zur Herstellung von Acrolein oder Acrylsäure oder deren Gemischen aus Propan |
US6623707B1 (en) * | 2000-06-19 | 2003-09-23 | Corning Incorporated | Monolithic catalyst dehydrogenation reactor |
RU2178399C1 (ru) * | 2000-12-09 | 2002-01-20 | Институт катализа им. Г.К. Борескова СО РАН | Способ каталитического дегидрирования углеводородов |
DE10211275A1 (de) | 2002-03-13 | 2003-09-25 | Basf Ag | Verfahren der kontinuierlichen heterogen katalysierten partiellen Dehydrierung |
US7271307B2 (en) * | 2002-10-29 | 2007-09-18 | Sud-Chemie Inc. | Method for improving the performance of a dehydrogenation catalyst |
DE10251135B4 (de) | 2002-10-31 | 2006-07-27 | Uhde Gmbh | Verfahren zur katalytischen Dehydrierung von leichten Paraffinen zu Olefinen |
DE102005010111A1 (de) | 2005-03-02 | 2006-09-07 | Basf Ag | Verfahren zur Herstellung von Acrylsäure durch heterogen katalysierte partielle Gasphasenoxidation von Propylen |
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 |
WO2006002713A1 (de) * | 2004-07-01 | 2006-01-12 | Basf Aktiengesellschaft | Verfahren zur herstellung von acrolein, oder acrylsäure oder deren gemisch aus propan |
KR101259649B1 (ko) | 2004-07-01 | 2013-04-30 | 바스프 에스이 | 프로필렌의 불균질 촉매화 부분 기상 산화를 사용한아크롤레인, 아크릴산 또는 그의 혼합물의 제조 방법 |
DE102004032129A1 (de) * | 2004-07-01 | 2005-03-03 | Basf Ag | Verfahren zur Herstellung von Acrolein, oder Acrylsäure oder deren Gemisch aus Propan |
DE102005009885A1 (de) | 2005-03-01 | 2006-09-14 | Basf Ag | Verfahren zur Herstellung von Acrolein oder Acrylsäure oder deren Gemisch durch heterogen katalysierte partielle Gasphasenoxidation von Propylen |
DE102005013039A1 (de) | 2005-03-18 | 2006-09-21 | Basf Ag | Verfahren zur Herstellung von Acrolein, oder Acrylsäure oder deren Gemisch aus Propan |
DE102004054657A1 (de) | 2004-11-11 | 2006-05-18 | Uhde Gmbh | Verfahren zur katalytischen Dehydrierung von Propan zu Propylen |
DE102005022798A1 (de) | 2005-05-12 | 2006-11-16 | Basf Ag | Verfahren zur Herstellung wenigstens eines Zielproduktes durch partielle Oxidation und/oder Ammoxidation von Propylen |
WO2007033934A2 (de) | 2005-09-20 | 2007-03-29 | Basf Se | Verfahren zur ermittlung der tortuosität, katalysatorträger, katalysator und verfahren zur dehydrierung von kohlenwasserstoffen |
DE102005044916A1 (de) | 2005-09-20 | 2007-03-22 | Basf Ag | Katalysatorträger, Katalysator und Verfahren zur Dehydrierung von Kohlenwasserstoffen |
DE102005052917A1 (de) | 2005-11-03 | 2007-10-11 | Basf Ag | Verfahren zur Herstellung von Acrolein, oder Acrylsäure oder deren Gemisch aus Propan |
US7388106B2 (en) | 2005-10-14 | 2008-06-17 | Basf Aktiengesellschaft | Process for preparing acrolein or acrylic acid or a mixture thereof from propane |
DE502006003491D1 (de) | 2005-11-03 | 2009-05-28 | Basf Se | Verfahren zum stabilen betreiben eines kontinuierlich ausgeübten herstellprozesses zur erzeugung von acrolein, oder acrylsäure oder deren gemisch aus propan |
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 |
KR101370749B1 (ko) | 2005-11-24 | 2014-03-06 | 바스프 에스이 | 프로판으로부터 아크롤레인 또는 아크릴산, 또는 그의혼합물의 제조 방법 |
DE102005057197A1 (de) | 2005-11-29 | 2007-06-06 | Basf Ag | Verfahren zur Herstellung von Acrolein, oder Acrylsäure, oder deren Gemisch aus Propan |
DE102005061626A1 (de) | 2005-12-21 | 2007-06-28 | Basf Ag | Verfahren der kontinuierlichen heterogen katalysierten partiellen Dehydrierung wenigstens eines zu dehydrierenden Kohlenwasserstoffs |
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 |
DE102006035718A1 (de) * | 2006-07-28 | 2008-01-31 | Basf Ag | Verfahren zum Langzeitbetrieb einer kontinuierlich betriebenen heterogen katalysierten partiellen Dehydrierung eines zu dehydrierenden Kohlenwasserstoffs |
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US20080045685A1 (en) | 2008-02-21 |
EP2049240B1 (de) | 2013-11-13 |
RU2009106952A (ru) | 2010-09-10 |
KR101422582B1 (ko) | 2014-07-24 |
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CN101495222A (zh) | 2009-07-29 |
US8642826B2 (en) | 2014-02-04 |
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RU2444400C2 (ru) | 2012-03-10 |
CN101495222B (zh) | 2012-03-21 |
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