CN101200476B - 用于过渡金属催化的加氢甲酰化的双亚磷酸酯配体 - Google Patents
用于过渡金属催化的加氢甲酰化的双亚磷酸酯配体 Download PDFInfo
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- CN101200476B CN101200476B CN200710199724.3A CN200710199724A CN101200476B CN 101200476 B CN101200476 B CN 101200476B CN 200710199724 A CN200710199724 A CN 200710199724A CN 101200476 B CN101200476 B CN 101200476B
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- phosphite
- hydroformylation
- metal
- glycol
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- 238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 60
- 239000003446 ligand Substances 0.000 title description 18
- 229910052723 transition metal Inorganic materials 0.000 title 1
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- 238000000034 method Methods 0.000 claims description 30
- 229910052703 rhodium Inorganic materials 0.000 claims description 27
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 26
- 229910052751 metal Inorganic materials 0.000 claims description 22
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- 239000011574 phosphorus Substances 0.000 claims description 19
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- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005669 hydrocyanation reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- YSWYYGKGAYSAOJ-UHFFFAOYSA-N phosphane Chemical compound P.P YSWYYGKGAYSAOJ-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000005538 phosphinite group Chemical group 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000012207 quantitative assay Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
- VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/185—Phosphorus; Compounds thereof with iron group metals or platinum group metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/06—Formation or introduction of functional groups containing oxygen of carbonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Description
配体 | 底物 | Rh[ppm] | 配体/铑 | 温度[℃] | 溶剂 | 压力[bar] | 转化率[%] | n-选择性[%] |
D-1 | 1-辛烯 | 38.4 | 5 | 120 | 甲苯 | 50 | 86 | 99 |
D-2 | 1-辛烯 | 38.4 | 5 | 100 | 甲苯 | 50 | 70 | 94 |
D-3 | 1-辛烯 | 38.4 | 5 | 100 | 甲苯 | 50 | 89 | 83 |
D-4 | 1-辛烯 | 40 | 5 | 100 | 甲苯 | 50 | 94 | 85 |
D-1 | n-辛烯类 | 96 | 5 | 120 | 甲苯 | 20 | 8 | 99 |
D-2 | n-辛烯类 | 96 | 5 | 120 | 甲苯 | 20 | 19 | 77 |
D-3 | n-辛烯类 | 96 | 10 | 120 | 甲苯 | 10 | 7 | 89 |
D-4 | n-辛烯类 | 96 | 5 | 120 | 甲苯 | 20 | 54 | 33 |
D-1 | 2-戊烯 | 96 | 5 | 120 | 甲苯 | 20 | 14 | 99 |
D-1 | 2-戊烯 | 96 | 2 | 120 | 甲苯 | 20 | 14 | 99 |
D-4 | 2-戊烯 | 96 | 5 | 120 | 甲苯 | 20 | 86 | 60 |
D-4 | 2-戊烯 | 96 | 2 | 120 | 甲苯 | 20 | 80 | 60 |
D-4a | 2-丁烯 | 90 | 4.8 | 90 | Texanol | 25 | 52 | 31 |
D-1c | 丙烯 | 40 | 5 | 90 | 甲苯 | 20 | 84 | 97 |
D-4b | 丙烯 | 90 | 4.1 | 70 | Texanol | 30 | 81 | 91 |
配体 | 底物 | Rh[ppm] | 配体/铑 | 温度[℃] | 溶剂 | 压力[bar] | 转化率[%] | n-选择性[%] |
D-1 | MODE | 40 | 5 | 100 | 甲苯 | 50 | 82 | 95 |
配体 | 时间[h] | 配体的31P-NMR-光谱纯度 |
D-1 | 0 | >99% |
D-1 | 2 | >99% |
D-1 | 144 | >99% |
D-2 | 0 | >95% |
D-2 | 2 | >95% |
D-2 | 144 | >95% |
D-4 | 0 | >99% |
D-4 | 2 | <5% |
D-4 | 144 | <1%a |
Claims (9)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102006058682.4 | 2006-12-13 | ||
DE102006058682A DE102006058682A1 (de) | 2006-12-13 | 2006-12-13 | Bisphosphitliganden für die übergangsmetallkatalysierte Hydroformylierung |
Publications (2)
Publication Number | Publication Date |
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CN101200476A CN101200476A (zh) | 2008-06-18 |
CN101200476B true CN101200476B (zh) | 2014-05-28 |
Family
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Application Number | Title | Priority Date | Filing Date |
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CN200710199724.3A Active CN101200476B (zh) | 2006-12-13 | 2007-12-12 | 用于过渡金属催化的加氢甲酰化的双亚磷酸酯配体 |
Country Status (10)
Country | Link |
---|---|
US (1) | US8003816B2 (zh) |
EP (1) | EP2091958B1 (zh) |
JP (1) | JP5593482B2 (zh) |
KR (1) | KR101468754B1 (zh) |
CN (1) | CN101200476B (zh) |
AT (1) | ATE507233T1 (zh) |
BR (1) | BRPI0720087A2 (zh) |
DE (2) | DE102006058682A1 (zh) |
WO (1) | WO2008071508A1 (zh) |
ZA (1) | ZA200904819B (zh) |
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DE102009026819A1 (de) | 2008-09-08 | 2010-03-11 | Evonik Röhm Gmbh | Monomermischung, Polymer, Beschichtungsmittel und Verfahren zur Herstellung einer Beschichtung |
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WO2012064586A1 (en) | 2010-11-12 | 2012-05-18 | Dow Technology Investments Llc | Mitigation of fouling in hydroformylation processes by water addition |
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WO2013184350A1 (en) | 2012-06-04 | 2013-12-12 | Dow Technology Investments Llc | Hydroformylation process |
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DE10140086A1 (de) | 2001-08-16 | 2003-02-27 | Oxeno Olefinchemie Gmbh | Neue Phosphitverbindungen und neue Phosphitmetallkomplexe |
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2006
- 2006-12-13 DE DE102006058682A patent/DE102006058682A1/de not_active Withdrawn
-
2007
- 2007-11-13 KR KR1020097012311A patent/KR101468754B1/ko active IP Right Grant
- 2007-11-13 US US12/515,967 patent/US8003816B2/en active Active
- 2007-11-13 EP EP07822522A patent/EP2091958B1/de active Active
- 2007-11-13 DE DE502007007088T patent/DE502007007088D1/de active Active
- 2007-11-13 WO PCT/EP2007/062248 patent/WO2008071508A1/de active Application Filing
- 2007-11-13 JP JP2009540686A patent/JP5593482B2/ja not_active Expired - Fee Related
- 2007-11-13 BR BRPI0720087-0A2A patent/BRPI0720087A2/pt not_active Application Discontinuation
- 2007-11-13 AT AT07822522T patent/ATE507233T1/de active
- 2007-12-12 CN CN200710199724.3A patent/CN101200476B/zh active Active
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2009
- 2009-07-09 ZA ZA200904819A patent/ZA200904819B/xx unknown
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Also Published As
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DE502007007088D1 (de) | 2011-06-09 |
US8003816B2 (en) | 2011-08-23 |
DE102006058682A1 (de) | 2008-06-19 |
JP2010513236A (ja) | 2010-04-30 |
ZA200904819B (en) | 2010-05-26 |
JP5593482B2 (ja) | 2014-09-24 |
BRPI0720087A2 (pt) | 2013-12-24 |
EP2091958A1 (de) | 2009-08-26 |
ATE507233T1 (de) | 2011-05-15 |
WO2008071508A1 (de) | 2008-06-19 |
KR20090088907A (ko) | 2009-08-20 |
US20100036143A1 (en) | 2010-02-11 |
KR101468754B1 (ko) | 2014-12-03 |
EP2091958B1 (de) | 2011-04-27 |
CN101200476A (zh) | 2008-06-18 |
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