JP5226922B2 - オレフィンのヒドロホルミル化のためのロジウム触媒の安定化 - Google Patents
オレフィンのヒドロホルミル化のためのロジウム触媒の安定化 Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims description 55
- 238000007037 hydroformylation reaction Methods 0.000 title claims description 31
- 150000001336 alkenes Chemical class 0.000 title claims description 27
- 229910052703 rhodium Inorganic materials 0.000 title claims description 24
- 239000010948 rhodium Substances 0.000 title claims description 24
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title claims description 23
- 230000006641 stabilisation Effects 0.000 title description 4
- 238000011105 stabilization Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims description 42
- 239000007789 gas Substances 0.000 claims description 27
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 17
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 16
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 239000007791 liquid phase Substances 0.000 claims description 15
- 238000003786 synthesis reaction Methods 0.000 claims description 14
- 238000000926 separation method Methods 0.000 claims description 12
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
- 239000012071 phase Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 239000011552 falling film Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- 230000000694 effects Effects 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- 150000001299 aldehydes Chemical class 0.000 description 8
- 239000003446 ligand Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 4
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- 239000012018 catalyst precursor Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 241001417501 Lobotidae Species 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 150000003284 rhodium compounds Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- LYSPDFZXVYQXTB-UHFFFAOYSA-N C1=CC=C(C=C1)O.[Rh] Chemical class C1=CC=C(C=C1)O.[Rh] LYSPDFZXVYQXTB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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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
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/40—Regeneration or reactivation
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
- B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
- B01J31/4046—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals containing rhodium
-
- 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
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Description
a)気相及び液相に分離させ、
b)液相を、反応していないオレフィン及びアルデヒドを含有する塔頂画分及びロジウム触媒を含有する塔底画分に分離させ、
c)塔底画分を、ヒドロホルミル化反応器の抽出物の温度より低い温度に冷却させ、これに一酸化炭素含有ガスを当てている。
工業用試験装置(図1)中で、以下のようにヒドロホルミル化させた:
気泡塔反応器(1)(容量60 l)中にオレフィン(10)、合成ガス(11)及び触媒溶液(21)を供給した。ヒドロホルミル化抽出物(13)を、フラッシュ(2)の中で放圧して5バールにした。漏出ガス(14)を、図示していない冷却中で冷却し、その際生じる縮合物を液体(15)と合わせた。フラッシュ容器(2)中で生じた液相(15)を、薄膜蒸発器(3)中で塔頂画分817)と塔底画分(16)とに分離する。この粗製生成物(17)を、冷却器(8)中で凝縮させ、容器(9)中で補修する。この塔底生成物(16)は、高沸点物中に溶解した触媒を含有しており、これを、冷却器(4)中で冷却させ(表3を見よ)、ポンプ(5)を用いて、中間容器(6)中に運搬する。容器(6)中で、合成ガス(18)を用いて圧力を10バールに調節する。容器(6)中の触媒溶液(16)の温度を、表3により定めた。触媒溶液(16)を、部分量(19)の除去及び触媒前駆物質(ロジウム化合物及び配位子)(20)の添加によって反応器(1)中の所望の活性にすることができ、溶液(21)として、ポンプ(7)を用いてヒドロホルミル化反応器81)に返送した。
(表3):
合成ガス圧に依存する触媒活性の低下
3 lのオートクレーブ(Buechi)中で、トルオール350g、トリス (2,4−ジ−第三ブチルーフェニル)ホスフィット3.03g及びオクタン酸ロジウム0.096gを、合成ガス(1/1 CO/H2)50バール、1時間、120℃で予備成形した。次に、サンプルを取り出し、触媒の活性を、第二のオートクレーブ中でシクロオクテンとのヒドロホルミル化反応(120℃、合成ガス圧50バール)で測定した。引き続き、この触媒に、第一のオートクレーブ中で数時間の期間に亘り熱負荷をかけ;前記の時間の間に、サンプルをとりだし、初期活性の測定の第と同様に触媒の活性を試験した。この試験を、種々の温度及び合成ガス圧で繰り返した。
Claims (7)
- ロジウム触媒を用いて相応するオレフィンをヒドロホルミル化することによって3〜21個の炭素原子を有するアルデヒドを製造する方法において、ヒドロホルミル化反応器の抽出物を、
a)気相及び液相に分離させ、この際、一酸化炭素分圧を0.5〜100バールに調節し、
b)液相を、反応していないオレフィン及びアルデヒドを含有する塔頂画分及びロジウム触媒を含有する塔底画分に分離させ、かつ、
c)塔底画分を、ヒドロホルミル化反応器の抽出物の温度より低い温度である10〜120℃の温度に冷却させ、これに0.1〜300バールの一酸化炭素分圧で一酸化炭素含有ガスを当て、かつ、これを完全にか又は部分的にヒドロホルミル化反応器に返送する、
ことを特徴とする、ロジウム触媒を用いて相応するオレフィンのヒドロホルミル化によって3〜21個の炭素原子を有するアルデヒドの製造法。
- 処理工程b)において、流下薄膜型蒸発器、薄層蒸発器、フラッシャー又は前記ユニットの組合せ物を用いる、請求項1に記載の方法。
- 処理工程b)における液相の平均滞留時間が15分未満である、請求項1または2に記載の方法。
- 処理工程b)における塔底画分の平均滞留時間が2分未満である、請求項1から3までのいずれか1項に記載の方法。
- 処理工程b)における温度が40〜180℃である、請求項1から4までのいずれか1項に記載の方法。
- 処理工程b)における圧力が0.01〜1バールである、請求項1から5までのいずれか1項に記載の方法。
- 一酸化炭素含有ガスとして、合成ガス、純粋な一酸化炭素又は一酸化炭素と窒素、メタン、水素及び/又は二酸化炭素とからなる混合物を使用する、請求項1から6までのいずれか1項に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10048301A DE10048301A1 (de) | 2000-09-29 | 2000-09-29 | Stabilisierung von Rhodiumkatalysatoren für die Hydroformylierung von Olefinen |
DE10048301.1 | 2000-09-29 |
Publications (2)
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JP2002161063A JP2002161063A (ja) | 2002-06-04 |
JP5226922B2 true JP5226922B2 (ja) | 2013-07-03 |
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JP2001300783A Expired - Fee Related JP5226922B2 (ja) | 2000-09-29 | 2001-09-28 | オレフィンのヒドロホルミル化のためのロジウム触媒の安定化 |
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Country | Link |
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US (1) | US6500991B2 (ja) |
EP (1) | EP1193239B1 (ja) |
JP (1) | JP5226922B2 (ja) |
KR (1) | KR100717984B1 (ja) |
CN (1) | CN1200923C (ja) |
AR (1) | AR030811A1 (ja) |
AT (1) | ATE284375T1 (ja) |
BR (1) | BR0104335A (ja) |
CA (1) | CA2357856A1 (ja) |
DE (2) | DE10048301A1 (ja) |
ES (1) | ES2231358T3 (ja) |
MX (1) | MXPA01009756A (ja) |
MY (1) | MY121533A (ja) |
PL (1) | PL201587B1 (ja) |
RU (1) | RU2270829C2 (ja) |
SA (1) | SA01220521B1 (ja) |
SG (1) | SG94863A1 (ja) |
TW (1) | TWI224094B (ja) |
ZA (1) | ZA200107977B (ja) |
Families Citing this family (49)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10058383A1 (de) * | 2000-11-24 | 2002-05-29 | Oxeno Olefinchemie Gmbh | Neue Phosphininverbindungen und deren Metallkomplexe |
EP1249438A1 (en) * | 2001-04-13 | 2002-10-16 | Dsm N.V. | Continuous hydroformylation process for producing an aldehyde |
BR0212835B1 (pt) * | 2001-09-26 | 2014-02-11 | Processos para preparação de misturas de ésteres dialquílicos de ácido ftálico isômeros | |
DE10149348A1 (de) | 2001-10-06 | 2003-04-10 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von 1-Olefin mit Palladiumcarbenverbindungen |
DE10210918B4 (de) | 2002-03-13 | 2004-06-03 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Bisphosphiten |
DE10220801A1 (de) | 2002-05-10 | 2003-11-20 | Oxeno Olefinchemie Gmbh | Verfahren zur Rhodium-katalysierten Hydroformylierung von Olefinen unter Reduzierung der Rhodiumverluste |
DE10223593A1 (de) * | 2002-05-27 | 2003-12-11 | Degussa | Hydroxydiphosphine und deren Verwendung in der Katalyse |
DE10225565A1 (de) | 2002-06-10 | 2003-12-18 | Oxeno Olefinchemie Gmbh | Katalysator und Verfahren zur Hydrierung von aromatischen Verbindungen |
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ZA200107977B (en) | 2002-05-29 |
KR100717984B1 (ko) | 2007-05-16 |
DE10048301A1 (de) | 2002-04-11 |
BR0104335A (pt) | 2002-05-07 |
JP2002161063A (ja) | 2002-06-04 |
SG94863A1 (en) | 2003-03-18 |
ES2231358T3 (es) | 2005-05-16 |
EP1193239A1 (de) | 2002-04-03 |
AR030811A1 (es) | 2003-09-03 |
PL349832A1 (en) | 2002-04-08 |
SA01220521B1 (ar) | 2006-05-23 |
DE50104749D1 (de) | 2005-01-13 |
US20020065437A1 (en) | 2002-05-30 |
RU2270829C2 (ru) | 2006-02-27 |
PL201587B1 (pl) | 2009-04-30 |
ATE284375T1 (de) | 2004-12-15 |
MY121533A (en) | 2006-01-28 |
KR20020025747A (ko) | 2002-04-04 |
CA2357856A1 (en) | 2002-03-29 |
EP1193239B1 (de) | 2004-12-08 |
CN1200923C (zh) | 2005-05-11 |
US6500991B2 (en) | 2002-12-31 |
CN1346821A (zh) | 2002-05-01 |
MXPA01009756A (es) | 2002-04-15 |
TWI224094B (en) | 2004-11-21 |
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