WO2000033956A1 - Catalyseur d'hydroformylation d'alcene - Google Patents

Catalyseur d'hydroformylation d'alcene Download PDF

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Publication number
WO2000033956A1
WO2000033956A1 PCT/GB1999/004062 GB9904062W WO0033956A1 WO 2000033956 A1 WO2000033956 A1 WO 2000033956A1 GB 9904062 W GB9904062 W GB 9904062W WO 0033956 A1 WO0033956 A1 WO 0033956A1
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WO
WIPO (PCT)
Prior art keywords
group
ligand
complex
catalyst
hydroformylation
Prior art date
Application number
PCT/GB1999/004062
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English (en)
Inventor
David Cole-Hamilton
Douglas Foster
David Gudmunsen
Eric George Hope
Alison Marion Stuart
Original Assignee
The University Court Of The University Of St Andrews
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from GBGB9826619.0A external-priority patent/GB9826619D0/en
Priority claimed from GBGB9902338.4A external-priority patent/GB9902338D0/en
Application filed by The University Court Of The University Of St Andrews filed Critical The University Court Of The University Of St Andrews
Priority to AU15744/00A priority Critical patent/AU1574400A/en
Publication of WO2000033956A1 publication Critical patent/WO2000033956A1/fr

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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
    • 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
    • B01J31/16—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
    • B01J31/1865—Phosphonites (RP(OR)2), their isomeric phosphinates (R2(RO)P=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
    • B01J31/16—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
    • 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
    • C07F15/0006—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
    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/141—Esters of phosphorous acids
    • C07F9/145—Esters of phosphorous acids with hydroxyaryl compounds
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
    • B01J2531/94—Fluorinated solvents
    • 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
    • B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
    • B01J2531/98—Phase-transfer catalysis in a mixed solvent system containing at least 2 immiscible solvents or solvent phases
    • 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
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/20—Non-coordinating groups comprising halogens
    • B01J2540/22—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate
    • B01J2540/225—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate comprising perfluoroalkyl groups or moieties
    • 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
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/60—Groups characterized by their function
    • B01J2540/64—Solubility enhancing groups

Definitions

  • the invention concerns an improved process for the hydroformylation of alkenes .
  • Hydroformylation is a major industrial process that involves the reaction of carbon monoxide and hydrogen with an alkene to give an aldehyde.
  • alkenes two products are possible depending upon the regioselectivity of the addition reaction.
  • the two products, linear (n) aldehyde and branched (i) aldehyde are generally obtained as a mixture but it is usually the linear product that is preferred for industrial applications.
  • the two reactions referred to above are both carried out in the homogeneous phase (i.e. the catalyst, substrate and products are all dissolved in a common solvent) and this means that a process is required for the separation of products, solvent and catalyst. Distillation is generally used, but the thermal sensitivity of the rhodium based catalysts means that they cannot be separated from longer chain aldehyde products (>C 4 ) .
  • One way of circumventing this problem is to use a two phase system with the catalyst dissolved in water. Since the substrate and products are immiscible in water, separation can be effected in a simple manner.
  • substrates with chain lengths of greater than 6 have such low solubility in water that the rate of the hydroformylation is too low for the aqueous process to be of commercial interest; and yet, it is just these substrates (C 9 -C 14 aldehydes) that are of interest for the production of soaps and detergents. Consequently the C 9 -C 14 aldehydes are currently manufactured using the older, less selective, more energy intensive cobalt based systems.
  • Desirable properties of such a system are that the reaction rate should be high (comparable to that with Rh/PPh 3 ) , that the rhodium content of the organic phase at the end of the reaction should be negligible and that the n:i ratio should be high, preferably using only a small amount of phosphine relative to rhodium.
  • EP-A-0, 633, 062 describes the use of [Rh(C0 2 ) (acetylacetonate) ] with either P [CH 2 CH 2 (CF 2 ) 5 CF 3 ] 3 or P[OCH 2 CH 2 (CF 2 ) 7 CF 3 ] 3 at a P:Rh ratio of 40:1.
  • the invention concerns new Iigands for use in the fiuorous biphasic hydroformylation of alkenes, which Iigands allow the reaction to occur at rates similar to those obtained using Rh/PPh 3 in organic solvents, which show little leaching of rhodium into the organic phase and which can provide high n:i ratios at low P:Rh loading.
  • the Iigands described herein also promote isomerisation of alkenes and can be used for the hydroformylation of internal alkenes giving significant amounts of n-aldehydes.
  • Iigands of general formula I when complexed to a rhodium centre are especially good at catalysis of alkene hydroformylation in a fiuorous multiphase system of the type described above.
  • the present invention provides a catalytic complex comprising a ligand of general formula I:
  • Ph is an optionally substituted phenyl ring; each group L independently represents a alkenyl group or other linker group;
  • each group Z represents a branched or linear fluorocarbon chain of up to 11 carbon atoms, preferably 3 to 9 carbon atoms ;
  • each group Y independently represents a group
  • each group Y may represent a C 1 -C 12 alkyl or aryl, which may optionally be substituted;
  • each a is 0 or 1;
  • each b is 0 or 1;
  • each m is an integer of from 1 to 5
  • said ligand is complexed directly or indirectly via the phosphorous moiety to a rhodium centre, for use in catalysis of hydroformylation of alkenes in a fiuorous multiphase system.
  • fiuorous multiphase system we mean a system including a liquid-liquid biphase where one phase is a fiuorous phase containing a fiuorous solvent (typically a fluorocarbon or a fluorohydrocarbon) .
  • a fiuorous solvent typically a fluorocarbon or a fluorohydrocarbon
  • Suitable solvents include fluorodimethylcyclohexane, perfluoromethylcyclohexane, hexafluorobenzene, pentafluorobenzene and the like.
  • the ligand of general formula I comprises a single fluorocarbon tail linked to a phenyl ring which is otherwise unsubstituted (apart from its connection to group X or to the phosphorous moiety) .
  • Group Z may represent a linear group -(CF 2 ) n - and n is an integer of from 3 to 11. Desirably integer n represents 3, 4, 5, 6, 7, 8 or 9. Generally Iigands where n represents 4, 5, 6 or 7 are most convenient.
  • the fluorocarbon tail (eg. -Z-CF 3 ) is required to adjust the solubility of the ligand in the fiuorous phase.
  • the exact number of fluorinated carbon atoms is not fixed, but may vary according to the reactants, solvents and other reaction conditions. If a single -Z-CF 3 tail is present, it may be located ortho, meta or para relative to the phosphorous linkage.
  • each group Y represents a group - (X) a -Ph- [ (L) b -Z-CF 3 ] m above, where X, Ph, L, b, Z and m are each as defined above.
  • Z represents a linear group -(CF 2 ) n - where n represents 4, 5, 6 or 7.
  • n represents 4, 5, 6 or 7.
  • la represents 1 and q represents 3) .
  • the present invention provides a catalyst for use in the catalysis of hydroformylation of an alkene, said catalyst comprising a ligand of general formula I (where X, Ph, n and m are as defined above) .
  • the ligand of said catalyst is described by general formula la (where n and m are as defined above, but n preferably represents 4, 5, 6 or 7 and m preferably represents 3) .
  • the catalyst described above is used in the hydroformylation of higher alkenes, that is alkenes of C 6 or above.
  • alkenes that is alkenes of C 6 or above.
  • C ⁇ - C 20 alkenes for example C 9 - C 14 ) are of most commercial interest.
  • the catalyst can either be prepared in situ by addition of the phosphorous based ligand (of Formula I above) to a rhodium containing precursor.
  • the catalyst may be provided as a pre-formed complex between the phosphorous ligand and rhodium. In the latter case excess phosphorous ligand may be added.
  • the rhodium catalytic complex may have the formula:
  • L 1 is a ligand of formula I above and d is an integer of 1 to 6;
  • c is an integer of 1 or more, preferably 1 to 6 , most preferably c is 1 or 2;
  • L 2 , L 3 , L 4 and L 5 are each Iigands attached to the rhodium and may be the same or different.
  • L 2 , L 3 , L 4 and L 5 may each independently represent a ligand according to formula 1 above, a halide (Cl, Br, F) , a carboxylate, 3-diketonate, alkoxide, ketone, open chain or cyclic ether, water, alcohol, sulphoxide, sulphalone, amide, a sulphur donor (such as a thiol, thiolate, dialkyl sulphide, heterocycle containing S, dialkylsulphoxide, dithiocarbamate, dithiophosphonate, dithiophosphate, xanthate, dithiocarbonate) ; a nitrogen donor (such as an amine, amide, nitrogen containing heterocycle, imine, nitric oxide) ; a phosphorous donor (such as mono- or di-prim
  • Iigands L 2 , L 3 , L 4 and 5 are each, independently, an integer of from 0 to 6. Any of Iigands L 2 , L 3 , L 4 and 5 may be joined to each other by a suitable bridging group.
  • rhodium containing precursor refers to a catalytic complex as described above to which a phosphorous ligand of formula I is to be added.
  • the rhodium containing precursor may be of formula :
  • the ligand of formula I may displace an existing ligand attached to the rhodium centre.
  • the present invention provides a process for hydroformylation of alkenes in a fiuorous multiphase system, said process comprising the step of adding a catalyst including a ligand of general formula I to the reactants.
  • the present invention provides a process for hydroformylation of alkenes in a fiuorous multiphase system, said process comprising the step of adding a ligand of formula I above and a rhodium precursor (as described above) to produce a catalyst in situ.
  • the ligand is described by general formula la.
  • the process relates to hydroformylation of higher (eg C 6 and above) alkenes, for example C 6 - C 20 alkenes.
  • C 9 - C 14 alkenes are of most commercial interest .
  • the P:Rh ratio is 20:1 or lower, preferably 12:1 or lower, for example 6:1 or even as low as 3:1.
  • the process further includes the step of recovering the catalytic complex by separating the fiuorous phase from the phase containing the reaction products.
  • Examples 1-12 Hydroformylation of Hex-1-ene
  • the solvents, rhodium complex and phosphorous containing compound were introduced in the autoclave under argon. C ⁇ /H 2 (total pressure 13 bar) was introduced and the autoclave heated with stirring to the reaction temperature. Hexene was contained in an injection unit between the autoclave and the mass flow controller. Once the conditions in the autoclave had stabilised, the tap between the injector and the autoclave was opened and gas from the ballast vessel allowed to pass through the mass flow controller to inject the hexene into the autoclave and bring the pressure in the autoclave to 20 bar. Readings of the pressure in the ballast vessel and the autoclave were taken every 5 seconds for approximately 1 hour. A typical reaction profile is shown in Figure 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical 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)

Abstract

L'invention concerne un complexe catalytique qui contient un ligand formant un complexe, directement ou indirectement par le biais d'une fraction phosphore, avec un centre en rhodium. Le complexe catalytique offre une meilleure catalyse d'hydroformylation d'alcène, de préférence une hydroformylation d'alcène en C9-C14, dans un système multiphases fluoritique. Le ligand de la présente invention est représenté par la formule générale (I), où X, Ph, L, Z, Y, a, b et m sont tels que définis dans la revendication 1. Les ligands privilégiés sont représentés par la formule générale (Ia), où Ph est un groupe phényle éventuellement substitué, Z est un groupe fluorocarbone en C1-C11, m vaut de 1 à 5 et q de 1 à 3.
PCT/GB1999/004062 1998-12-04 1999-12-03 Catalyseur d'hydroformylation d'alcene WO2000033956A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU15744/00A AU1574400A (en) 1998-12-04 1999-12-03 Alkene hydroformylation catalyst

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB9826619.0 1998-12-04
GBGB9826619.0A GB9826619D0 (en) 1998-12-04 1998-12-04 Catalyst
GB9902338.4 1999-02-03
GBGB9902338.4A GB9902338D0 (en) 1999-02-03 1999-02-03 Catalyst

Publications (1)

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WO2000033956A1 true WO2000033956A1 (fr) 2000-06-15

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6495186B1 (en) * 2001-09-26 2002-12-17 International Flavors & Fragrances Inc. Use of 4-ethyloctanal in perfume and flavor compositions
US6495497B1 (en) * 2001-09-26 2002-12-17 International Flavors & Fragrances Inc. Use of 4-ethyloctanal in perfume compositions
US7404943B2 (en) 2001-05-30 2008-07-29 The Regents Of The University Of California Methods for solubilizing and recovering fluorinated compounds
US10625249B2 (en) 2016-04-14 2020-04-21 Technische Universität Berlin Catalyst for the hydroformylation of olefins, and use thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0633062A1 (fr) * 1993-07-08 1995-01-11 Exxon Research And Engineering Company Catalyseur ou système réactif fluoré et multiphase ainsi qu'un procédé pour son utilisation
DE19702025A1 (de) * 1997-01-23 1998-07-30 Studiengesellschaft Kohle Mbh Verwendung perfluoralkylsubstituierter Phosphorverbindungen als Liganden für die homogene Katalyse in überkritischem Kohlendioxid

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0633062A1 (fr) * 1993-07-08 1995-01-11 Exxon Research And Engineering Company Catalyseur ou système réactif fluoré et multiphase ainsi qu'un procédé pour son utilisation
DE19702025A1 (de) * 1997-01-23 1998-07-30 Studiengesellschaft Kohle Mbh Verwendung perfluoralkylsubstituierter Phosphorverbindungen als Liganden für die homogene Katalyse in überkritischem Kohlendioxid

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
P. BHATTACHARYYA ET AL.: "Phosphorus(III) ligands with fluorous ponytails", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1., 1997, CHEMICAL SOCIETY. LETCHWORTH., GB, pages 3609 - 3612, XP002131617, ISSN: 0300-922X *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7404943B2 (en) 2001-05-30 2008-07-29 The Regents Of The University Of California Methods for solubilizing and recovering fluorinated compounds
US6495186B1 (en) * 2001-09-26 2002-12-17 International Flavors & Fragrances Inc. Use of 4-ethyloctanal in perfume and flavor compositions
US6495497B1 (en) * 2001-09-26 2002-12-17 International Flavors & Fragrances Inc. Use of 4-ethyloctanal in perfume compositions
US10625249B2 (en) 2016-04-14 2020-04-21 Technische Universität Berlin Catalyst for the hydroformylation of olefins, and use thereof

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