CN1688593A - 双螯合配体及其在羰基化方法中的用途 - Google Patents
双螯合配体及其在羰基化方法中的用途 Download PDFInfo
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- CN1688593A CN1688593A CN03824189.7A CN03824189A CN1688593A CN 1688593 A CN1688593 A CN 1688593A CN 03824189 A CN03824189 A CN 03824189A CN 1688593 A CN1688593 A CN 1688593A
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- phenylene
- alkyl
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- 238000000034 method Methods 0.000 title claims abstract description 124
- 238000005810 carbonylation reaction Methods 0.000 title claims abstract description 72
- 230000006315 carbonylation Effects 0.000 title claims abstract description 70
- 239000003446 ligand Substances 0.000 title claims abstract description 62
- 230000008569 process Effects 0.000 title claims abstract description 42
- -1 hydrocarbyl radicals Chemical class 0.000 claims abstract description 112
- 239000000203 mixture Substances 0.000 claims abstract description 90
- 239000001257 hydrogen Substances 0.000 claims abstract description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 52
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000003118 aryl group Chemical group 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 125000004429 atom Chemical group 0.000 claims abstract description 6
- 229910052723 transition metal Inorganic materials 0.000 claims description 53
- 150000003624 transition metals Chemical class 0.000 claims description 53
- 238000007037 hydroformylation reaction Methods 0.000 claims description 52
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical group [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 38
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 29
- 239000010948 rhodium Substances 0.000 claims description 28
- 150000001336 alkenes Chemical class 0.000 claims description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 21
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 17
- 229910052698 phosphorus Inorganic materials 0.000 claims description 17
- 229910052703 rhodium Inorganic materials 0.000 claims description 17
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 17
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 15
- 239000011574 phosphorus Substances 0.000 claims description 15
- 239000012018 catalyst precursor Substances 0.000 claims description 14
- 150000004646 arylidenes Chemical group 0.000 claims description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
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- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 claims description 8
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
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- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
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- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
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- 229910052741 iridium Inorganic materials 0.000 claims description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- 150000003623 transition metal compounds Chemical class 0.000 claims description 5
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 4
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- MEKDJHLCEWXIOB-UHFFFAOYSA-N IC1(CC(C(=O)O)=CC(=C1)C)C(=O)O Chemical compound IC1(CC(C(=O)O)=CC(=C1)C)C(=O)O MEKDJHLCEWXIOB-UHFFFAOYSA-N 0.000 claims description 4
- DZUQMMBTRWSTJJ-UHFFFAOYSA-N acetic acid;but-1-ene Chemical class CCC=C.CC(O)=O DZUQMMBTRWSTJJ-UHFFFAOYSA-N 0.000 claims description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052785 arsenic Inorganic materials 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
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- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
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- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
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- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 claims description 2
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- NMWLAAVSUGFWNX-UHFFFAOYSA-N CCCCC1=C(C=CC(=C1)OC)C2=CC=C(C=C2)OC Chemical group CCCCC1=C(C=CC(=C1)OC)C2=CC=C(C=C2)OC NMWLAAVSUGFWNX-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000004448 titration Methods 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
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Classifications
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
-
- 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
- B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
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- 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
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
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- 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
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- 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
- B01J2531/821—Ruthenium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- 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
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- 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
- B01J2531/827—Iridium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
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- General Health & Medical Sciences (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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Abstract
Description
配体 | L/Rh(摩尔比) | 正壬醛(mol%) | 异壬醛(mol%) | 异构化(mol%)3 | 初始速率(M/hr) |
A1 | 1.3/1 | 92.9 | 1.7 | 5.4 | 4.0 |
A2 | 1.3/1 | 93.9 | 2.4 | 3.7 | 1.8 |
D1 | 1.5/1 | 90.7 | 0.8 | 8.5 | 18 |
配体 | L/Rh(摩尔比) | 1,2,3,4-THBA(mol%) | 初始速率(M/hr) |
E | 1.2/1 | 97 | 16 |
Claims (46)
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US41862002P | 2002-10-15 | 2002-10-15 | |
US60/418,620 | 2002-10-15 |
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CN1688593A true CN1688593A (zh) | 2005-10-26 |
CN100418974C CN100418974C (zh) | 2008-09-17 |
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CNB038241897A Expired - Lifetime CN100418974C (zh) | 2002-10-15 | 2003-09-26 | 双螯合配体及其在羰基化方法中的用途 |
Country Status (9)
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US (1) | US7294729B2 (zh) |
EP (1) | EP1554293B1 (zh) |
JP (1) | JP2006503086A (zh) |
CN (1) | CN100418974C (zh) |
AT (1) | ATE388956T1 (zh) |
AU (1) | AU2003270902A1 (zh) |
BR (1) | BR0314566A (zh) |
DE (1) | DE60319725T2 (zh) |
WO (1) | WO2004035595A1 (zh) |
Families Citing this family (8)
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CN1639177B (zh) | 2002-03-11 | 2010-05-05 | 陶氏技术投资有限责任公司 | 用于羰基化过程的双亚磷酸酯 |
EP2308817B1 (en) * | 2003-07-03 | 2016-10-05 | Dow Technology Investments LLC | Minimization of ligand degradation products, or reversion of same to useful phosphine ligands |
US20080027218A1 (en) * | 2004-04-29 | 2008-01-31 | Daugs Edward D | Hydroformylation Process for Pharmaceutical Intermediate |
DE102004049339A1 (de) * | 2004-10-08 | 2006-04-13 | Basf Ag | Verfahren zur Reinigung von phosphorhaltigen Chelat-Liganden |
WO2007114445A1 (ja) * | 2006-04-04 | 2007-10-11 | Kuraray Co., Ltd. | ビスホスファイトおよび第8~10族金属化合物を用いたアルデヒドの製造方法、並びに該ビスホスファイト |
CN101443302B (zh) * | 2006-05-15 | 2013-04-10 | 陶氏环球技术有限责任公司 | 具有改良铑回收的加氢甲酰基化方法和产品分离 |
DE102006058682A1 (de) * | 2006-12-13 | 2008-06-19 | Evonik Oxeno Gmbh | Bisphosphitliganden für die übergangsmetallkatalysierte Hydroformylierung |
US7906688B2 (en) * | 2007-04-05 | 2011-03-15 | Dow Global Technologies Inc. | Calixarene bisphosphite ligand for use in hydroformylation processes |
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DE19836807A1 (de) | 1998-08-14 | 2000-02-17 | Basf Ag | Verfahren zur Herstellung von Aldehyden und/oder Alkoholen oder Aminen |
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CN1639177B (zh) * | 2002-03-11 | 2010-05-05 | 陶氏技术投资有限责任公司 | 用于羰基化过程的双亚磷酸酯 |
JP4608860B2 (ja) * | 2002-08-30 | 2011-01-12 | 三菱化学株式会社 | アリル化合物の製造方法及び縮合系共重合体 |
-
2003
- 2003-09-26 US US10/527,568 patent/US7294729B2/en active Active
- 2003-09-26 WO PCT/US2003/030380 patent/WO2004035595A1/en active Application Filing
- 2003-09-26 CN CNB038241897A patent/CN100418974C/zh not_active Expired - Lifetime
- 2003-09-26 EP EP03752616A patent/EP1554293B1/en not_active Expired - Lifetime
- 2003-09-26 JP JP2004544772A patent/JP2006503086A/ja active Pending
- 2003-09-26 BR BRPI0314566-2A patent/BR0314566A/pt unknown
- 2003-09-26 DE DE60319725T patent/DE60319725T2/de not_active Expired - Lifetime
- 2003-09-26 AU AU2003270902A patent/AU2003270902A1/en not_active Abandoned
- 2003-09-26 AT AT03752616T patent/ATE388956T1/de not_active IP Right Cessation
Also Published As
Publication number | Publication date |
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AU2003270902A1 (en) | 2004-05-04 |
JP2006503086A (ja) | 2006-01-26 |
DE60319725T2 (de) | 2009-01-29 |
WO2004035595A1 (en) | 2004-04-29 |
ATE388956T1 (de) | 2008-03-15 |
BR0314566A (pt) | 2006-06-27 |
EP1554293A1 (en) | 2005-07-20 |
DE60319725D1 (de) | 2008-04-24 |
EP1554293B1 (en) | 2008-03-12 |
US7294729B2 (en) | 2007-11-13 |
CN100418974C (zh) | 2008-09-17 |
US20060058557A1 (en) | 2006-03-16 |
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