GB1109787A - New phosphine derivatives and their use in the hydroformylation of olefinic compounds - Google Patents
New phosphine derivatives and their use in the hydroformylation of olefinic compoundsInfo
- Publication number
- GB1109787A GB1109787A GB13556/66A GB1355666A GB1109787A GB 1109787 A GB1109787 A GB 1109787A GB 13556/66 A GB13556/66 A GB 13556/66A GB 1355666 A GB1355666 A GB 1355666A GB 1109787 A GB1109787 A GB 1109787A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphines
- carbon atoms
- tertiary
- phosphine
- heterocyclic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003003 phosphines Chemical class 0.000 title abstract 6
- 238000007037 hydroformylation reaction Methods 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 title abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 13
- -1 6-membered heterocyclic phosphines Chemical group 0.000 abstract 11
- 125000004432 carbon atom Chemical group C* 0.000 abstract 10
- 239000003054 catalyst Substances 0.000 abstract 9
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 7
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 4
- 239000003446 ligand Substances 0.000 abstract 4
- 229910052698 phosphorus Inorganic materials 0.000 abstract 4
- 150000003254 radicals Chemical class 0.000 abstract 4
- 150000001298 alcohols Chemical class 0.000 abstract 3
- 229910017052 cobalt Inorganic materials 0.000 abstract 3
- 239000010941 cobalt Substances 0.000 abstract 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 125000004437 phosphorous atom Chemical group 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000002619 bicyclic group Chemical group 0.000 abstract 2
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 abstract 1
- WQLOTEVPEXXLGP-UHFFFAOYSA-N C(=O)=C1C(C(C2CCC(C1)P2C2=CC=CC=C2)=C=O)=C=O.[Co] Chemical compound C(=O)=C1C(C(C2CCC(C1)P2C2=CC=CC=C2)=C=O)=C=O.[Co] WQLOTEVPEXXLGP-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 abstract 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 150000001868 cobalt Chemical class 0.000 abstract 1
- 150000001923 cyclic compounds Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000001993 dienes Chemical class 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000005673 monoalkenes Chemical class 0.000 abstract 1
- 125000005474 octanoate group Chemical class 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 abstract 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
Classifications
-
- 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
- B01J31/20—Carbonyls
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2461—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as ring members in the condensed ring system or in a further ring
- B01J31/248—Bridged ring systems, e.g. 9-phosphabicyclononane
-
- 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
-
- 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
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- 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
- C07F9/6568—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 atoms as the only ring hetero atoms
- C07F9/65683—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 atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
-
- 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
- C07F9/6568—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 atoms as the only ring hetero atoms
- C07F9/65685—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 atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- 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
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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
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/061—Metal salts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44370365A | 1965-03-29 | 1965-03-29 | |
| US46857365A | 1965-06-30 | 1965-06-30 | |
| US46857465A | 1965-06-30 | 1965-06-30 | |
| US46857565A | 1965-06-30 | 1965-06-30 | |
| US468572A US3400163A (en) | 1965-06-30 | 1965-06-30 | Bicyclic heterocyclic sec- and tert-phosphines |
| US49355565A | 1965-10-06 | 1965-10-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1109787A true GB1109787A (en) | 1968-04-18 |
Family
ID=27559997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13556/66A Expired GB1109787A (en) | 1965-03-29 | 1966-03-28 | New phosphine derivatives and their use in the hydroformylation of olefinic compounds |
Country Status (6)
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1768391B1 (de) * | 1968-05-09 | 1971-08-26 | Basf Ag | Verfahren zur Herstellung von Aldehyden und Alkoho |
| US5585004A (en) * | 1991-09-18 | 1996-12-17 | Imperial College Of Science Technology & Medicine | Treatment of aqueous media containing organic material using tubular membranes |
| US5681473A (en) * | 1995-05-01 | 1997-10-28 | Union Carbide Chemicals & Plastics Technology Corporation | Membrane separation process |
| WO2002014248A2 (en) * | 2000-08-14 | 2002-02-21 | Sasol Technology (Proprietary) Limited | Bicyclic phosphin comprising hydroformylation catalyst and use thereof in production of oxygenated products |
| WO2003053572A1 (de) * | 2001-12-21 | 2003-07-03 | Basf Aktiengesellschaft | Verfahren zur hydroformylierung in gegenwart eines polymeren liganden mit phosphacyclohexan-strukturlementen |
| WO2003068719A2 (en) * | 2002-02-13 | 2003-08-21 | Sasol Technology (Proprietary) Limited | Production of oxygenated products |
| WO2004005223A1 (en) * | 2002-07-05 | 2004-01-15 | Sasol Technology (Uk) Ltd | Phosphorus containing ligands for metathesis catalysts |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3502730A (en) * | 1965-03-29 | 1970-03-24 | Shell Oil Co | Heterocyclic phosphine oxides |
| GB1127965A (en) * | 1965-11-26 | 1968-09-25 | Shell Int Research | Ditertiary phosphines and application thereof as catalyst components for alcohol production |
| US3665947A (en) * | 1970-01-05 | 1972-05-30 | Bendix Corp | Fluidic sensing circuit and pressure regulator |
| US3859369A (en) * | 1971-07-26 | 1975-01-07 | Du Pont | Process for the production of 2-methyl-1,4-butanediol |
| US4005112A (en) * | 1973-11-30 | 1977-01-25 | General Electric Company | Multistep method for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid |
| US4005113A (en) * | 1973-12-03 | 1977-01-25 | General Electric Company | Multi-step process for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid |
| EP0024761A1 (en) * | 1979-08-29 | 1981-03-11 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of alcohols or aldehydes, alcohols or aldehydes prepared by this process and stabilized compositions suitable for use in the said process |
| US5112519A (en) * | 1989-06-05 | 1992-05-12 | Mobil Oil Corporation | Process for production of biodegradable surfactants and compositions thereof |
| US6756411B2 (en) | 1995-06-29 | 2004-06-29 | Sasol Technology (Proprietary) Limited | Process for producing oxygenated products |
| US6150322A (en) * | 1998-08-12 | 2000-11-21 | Shell Oil Company | Highly branched primary alcohol compositions and biodegradable detergents made therefrom |
| US5849960A (en) * | 1996-11-26 | 1998-12-15 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
| US5780694A (en) | 1996-11-26 | 1998-07-14 | Shell Oil Company | Dimerized alcohol compositions and biodegradible surfactants made therefrom having cold water detergency |
| US6765106B2 (en) | 2001-02-15 | 2004-07-20 | Shell Oil Company | Process for preparing a branched olefin, a method of using the branched olefin for making a surfactant, and a surfactant |
| US6747165B2 (en) * | 2001-02-15 | 2004-06-08 | Shell Oil Company | Process for preparing (branched-alkyl) arylsulfonates and a (branched-alkyl) arylsulfonate composition |
| MY128880A (en) | 2001-06-12 | 2007-02-28 | Shell Int Research | Process for the preparation of a highly liear alcohol composition |
| WO2003080550A1 (en) | 2001-11-14 | 2003-10-02 | Shell Internationale Research Maatschappij B.V. | Hydroformylation process |
| US7148388B2 (en) * | 2002-03-29 | 2006-12-12 | Exxonmobil Chemical Patents Inc. | Process for preparing and olefinic hydrocarbon mixture |
| US7507868B2 (en) * | 2002-03-29 | 2009-03-24 | Exxonmobil Chemical Patents Inc. | Olefin oligomerization process |
| DE60315351T2 (de) * | 2002-12-19 | 2008-05-08 | Shell Internationale Research Maatschappij B.V. | Hydroformulierungsreaktion in anwesenheit von schwefel enthaltenden additiven |
| US20040176655A1 (en) * | 2003-02-05 | 2004-09-09 | Ayoub Paul Marie | Methods of preparing branched alkyl aromatic hydrocarbons |
| US7335802B2 (en) * | 2003-10-15 | 2008-02-26 | Shell Oil Company | Methods of preparing branched aliphatic alcohols |
| US7329783B2 (en) * | 2005-06-30 | 2008-02-12 | Shell Oil Company | Hydroformylation process |
| WO2008000808A1 (en) * | 2006-06-30 | 2008-01-03 | Shell Internationale Research Maatschappij B.V. | Catalytic reaction process |
| US7858787B2 (en) * | 2006-09-22 | 2010-12-28 | Shell Oil Company | Process for producing olefins |
| CN101589012B (zh) * | 2006-12-21 | 2012-08-22 | 国际壳牌研究有限公司 | 加氢甲酰化方法 |
| US8017811B2 (en) * | 2007-05-23 | 2011-09-13 | Shell Oil Company | Hydroformylation process |
| US8017810B2 (en) * | 2007-05-23 | 2011-09-13 | Shell Oil Company | Hydroformulation process |
| US7767862B2 (en) * | 2008-08-11 | 2010-08-03 | Shell Oil Company | Ligand, catalyst and process for hydroformylation |
| US8232431B2 (en) * | 2008-09-22 | 2012-07-31 | The Procter & Gamble Company | Specific branched surfactants and consumer products |
| EP2650275A1 (en) | 2008-09-22 | 2013-10-16 | The Procter & Gamble Company | Specific polybranched alcohols and consumer products based thereon |
| US8383869B2 (en) | 2009-09-01 | 2013-02-26 | Shell Oil Company | Olefin oligomer composition |
| WO2012072594A1 (en) | 2010-11-30 | 2012-06-07 | Shell Internationale Research Maatschappij B.V. | Ligand, catalyst and process for hydroformylation |
| WO2012091880A2 (en) | 2010-12-29 | 2012-07-05 | Shell Oil Company | Method and composition for enhanced hydrocarbons recovery from a formation containing a crude oil |
| US9150492B2 (en) | 2011-06-01 | 2015-10-06 | Shell Oil Company | Nonyl alcohols with a low degree of branching and their derivatives |
| US9067861B1 (en) | 2011-12-27 | 2015-06-30 | Shell Oil Company | Process for the production of alcohols |
| US9012694B2 (en) | 2011-12-27 | 2015-04-21 | Shell Oil Company | Process for the production of alcohols |
| WO2013144735A1 (en) | 2012-03-26 | 2013-10-03 | Sasol Technology (Proprietary) Limited | Conversion of a mixture of c2 - and c3 -olefins to butanol |
| CA2874534A1 (en) | 2012-05-29 | 2013-12-05 | Shell Internationale Research Maatschappij B.V. | A laundry detergent composition and method of making thereof |
| WO2014140353A1 (en) * | 2013-03-14 | 2014-09-18 | Dublin City University | Methods for phosphine oxide reduction in catalytic wittig reactions |
| US9828565B2 (en) | 2015-12-22 | 2017-11-28 | Shell Oil Company | Alcohol composition and derivatives thereof |
| US9828573B2 (en) | 2015-12-22 | 2017-11-28 | Shell Oil Company | Alcohol composition and derivatives thereof |
| WO2018132626A1 (en) | 2017-01-13 | 2018-07-19 | The Procter & Gamble Company | Compositions comprising branched sulfonated surfactants |
| EP3424895A1 (de) | 2017-07-06 | 2019-01-09 | Rheinisch-Westfälische Technische Hochschule (RWTH) Aachen | Verfahren zur herstellung eines treibstoffes für verbrennungsmotoren |
| CN114426469B (zh) * | 2020-09-28 | 2024-07-09 | 中国石油化工股份有限公司 | 一种烯烃氢甲酰化制备醇和醛的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2564130A (en) * | 1948-07-24 | 1951-08-14 | Du Pont | One-step butyl alcohol process |
| NL146830C (US07122547-20061017-C00032.png) * | 1960-07-22 | |||
| US3239569A (en) * | 1960-07-22 | 1966-03-08 | Shell Oil Co | Hydroformylation of olefins |
| US3310576A (en) * | 1963-02-05 | 1967-03-21 | Exxon Research Engineering Co | Hydroformylation catalyst and process relating thereto |
-
1965
- 1965-06-30 US US468573A patent/US3420898A/en not_active Expired - Lifetime
- 1965-10-06 US US493555A patent/US3440291A/en not_active Expired - Lifetime
-
1966
- 1966-03-28 GB GB13556/66A patent/GB1109787A/en not_active Expired
- 1966-03-28 SE SE4084/66A patent/SE345254B/xx unknown
- 1966-03-28 SE SE01919/70A patent/SE356692B/xx unknown
- 1966-03-28 DE DE19661543471 patent/DE1543471A1/de active Granted
- 1966-03-28 DE DE19661667286 patent/DE1667286B2/de active Granted
- 1966-03-29 BE BE678614D patent/BE678614A/xx not_active IP Right Cessation
- 1966-03-29 NL NL666604094A patent/NL145534B/xx not_active IP Right Cessation
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1768391B1 (de) * | 1968-05-09 | 1971-08-26 | Basf Ag | Verfahren zur Herstellung von Aldehyden und Alkoho |
| US5585004A (en) * | 1991-09-18 | 1996-12-17 | Imperial College Of Science Technology & Medicine | Treatment of aqueous media containing organic material using tubular membranes |
| US5681473A (en) * | 1995-05-01 | 1997-10-28 | Union Carbide Chemicals & Plastics Technology Corporation | Membrane separation process |
| JP2004506032A (ja) * | 2000-08-14 | 2004-02-26 | サソール テクノロジー（プロプライエタリー）リミテッド | 含酸素製品の製造 |
| WO2002014248A2 (en) * | 2000-08-14 | 2002-02-21 | Sasol Technology (Proprietary) Limited | Bicyclic phosphin comprising hydroformylation catalyst and use thereof in production of oxygenated products |
| WO2002014248A3 (en) * | 2000-08-14 | 2002-07-04 | Sasol Tech Pty Ltd | Bicyclic phosphin comprising hydroformylation catalyst and use thereof in production of oxygenated products |
| CN1327962C (zh) * | 2000-08-14 | 2007-07-25 | 萨索尔技术(控股)有限公司 | 含氧产品的生产方法 |
| US6717018B2 (en) | 2000-08-14 | 2004-04-06 | Sasol Technology (Proprietary) Limited | Production of oxygenated products |
| WO2003053572A1 (de) * | 2001-12-21 | 2003-07-03 | Basf Aktiengesellschaft | Verfahren zur hydroformylierung in gegenwart eines polymeren liganden mit phosphacyclohexan-strukturlementen |
| WO2003068719A2 (en) * | 2002-02-13 | 2003-08-21 | Sasol Technology (Proprietary) Limited | Production of oxygenated products |
| WO2003068719A3 (en) * | 2002-02-13 | 2003-12-18 | Sasol Tech Pty Ltd | Production of oxygenated products |
| WO2003068786A1 (en) * | 2002-02-13 | 2003-08-21 | Cytec Technology Corp | Phosphine compounds |
| WO2004005223A1 (en) * | 2002-07-05 | 2004-01-15 | Sasol Technology (Uk) Ltd | Phosphorus containing ligands for metathesis catalysts |
| US7276616B2 (en) | 2002-07-05 | 2007-10-02 | Sasol Technology (Uk) Limited | Phosphorous containing ligands for metathesis catalysts |
Also Published As
| Publication number | Publication date |
|---|---|
| NL145534B (nl) | 1975-04-15 |
| SE345254B (US07122547-20061017-C00032.png) | 1972-05-23 |
| BE678614A (US07122547-20061017-C00032.png) | 1966-09-29 |
| SE356692B (US07122547-20061017-C00032.png) | 1973-06-04 |
| DE1667286C3 (US07122547-20061017-C00032.png) | 1973-10-11 |
| DE1667286B2 (de) | 1973-03-08 |
| DE1543471A1 (de) | 1969-08-21 |
| DE1667286A1 (de) | 1971-05-19 |
| US3440291A (en) | 1969-04-22 |
| NL6604094A (US07122547-20061017-C00032.png) | 1966-09-30 |
| US3420898A (en) | 1969-01-07 |
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