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WO2018147793A1 - Procédé de carbonylation et composition de ligand comprenant un ligand de phosphite bidenté et un anti-oxydant de phosphine tertiaire - Google Patents

Procédé de carbonylation et composition de ligand comprenant un ligand de phosphite bidenté et un anti-oxydant de phosphine tertiaire Download PDF

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Publication number
WO2018147793A1
WO2018147793A1 PCT/SE2018/050120 SE2018050120W WO2018147793A1 WO 2018147793 A1 WO2018147793 A1 WO 2018147793A1 SE 2018050120 W SE2018050120 W SE 2018050120W WO 2018147793 A1 WO2018147793 A1 WO 2018147793A1
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ligand
formula
group
process according
phosphine
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Ian MUNSLOW
Matias KANGAS
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Perstorp AB
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Perstorp AB
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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
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/86—Use of additives, e.g. for stabilisation
    • 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
    • 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
    • B01J31/24—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
    • 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
    • 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
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
    • 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
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • 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
    • 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

Definitions

  • the present invention refers to a carbonylation, such as a hydroformylation, process in presence of a syngas comprising carbon monoxide and hydrogen, at least one Group VIII transition metal catalyst or catalyst precursor and at least one ligand mixture comprising at least one phosphite ligand of Formula (I) and at least one anti-oxidant selected among tertiary phosphines.
  • a carbonylation such as a hydroformylation
  • Industrial processes such as carbonylation reactions including hydroformylations and cyclohydrocarbonylations of functionalised and unfunctionalised alkenes, alkadienes, and alkynes for production of commodity chemicals and speciality chemicals often use as catalysts Group VIII transition metals complexed with one or more ligands, such as organophosphines and organophosphites.
  • Carbonylation processes directed to production of oxygenated products, in the presence of catalysts in general involve the reaction of an organic compound with carbon monoxide and optionally at least one other reactant and are well known in the art.
  • Said processes include the carbonylation of organic compounds, such as olefins, acetylenes, alcohols and activated chlorides, with carbon monoxide alone or with carbon monoxide and either hydrogen, alcohol, amine, water or a reducing agent, as well as ring closure reactions of functional unsaturated compounds, for instance unsaturated amides, with carbon monoxide.
  • organic compounds such as olefins, acetylenes, alcohols and activated chlorides
  • carbon monoxide alone or with carbon monoxide and either hydrogen, alcohol, amine, water or a reducing agent
  • ring closure reactions of functional unsaturated compounds for instance unsaturated amides
  • a major type of known carbonylation reactions is hydroformylations of olefinic compounds with carbon monoxide and hydrogen to produce oxygenated products, such as aldehydes, using Group VIII transition metals complexed with phosphorus ligands, wherein the phosphorus ligands typically are organophosphines and/
  • Hydroformylation is the general term applied to the reaction of an olefinic substrate with carbon monoxide and hydrogen and/or a reducing agent to form aldehydes having one carbon atom more than the original olefinic reactant as illustrated by Scheme 1 below.
  • R is a hydrocarbyl residue optionally comprising functional groups, such as carboxyl, hydroxyl and/or ester groups.
  • oxo process hydroformylation of olefins in the presence of transition metal catalyst complexes. Yielded aldehydes can for instance be hydrogenated to give so called oxo alcohols and long-chain products can be converted into sulphonates and used as detergents. The oxo process was discovered in 1938 by Roelen and coworkers of Ruhr Chemie. The first catalysts, and still used on a large scale, were cobalt carbonyl complexes formed from [HCo(CO) 4 ].
  • -R , -R , -R , -R , R , R and R individually is hydrogen or a linear or branched alkyl group and -Ar is a substituted or unsubstituted aryl group, such as a group of Formula (II) or (III)
  • organophosphite ligands tend to readily oxidize on addition to a reaction mixture and/or during storage, with between roughly 1/4 and 1/3 or even more of these ligands oxidized, thus reducing the active amount of said ligand and thus implying for instance reduced catalytic effect, reduced processing efficiency, altered selectivity and/or yield. Said oxidation also implies addition of larger than optimum amounts of ligand to compensate for oxidized material, thus implying unnecessary high costs.
  • organophosphite ligand oxidation problem by adding a second phosphorous-based compound.
  • W 02010117391 discloses a hydroformylation process conducted in the presence of a mixture of an organopolyphosphite ligand and an organomonophosphine ligand forming a transition metal ligand complex hydroformylation catalyst.
  • the molar ratio of both the organomonophosphine and the organopolyphosphite to the metal being at least 1.
  • RU2584952 discloses a hydride-carbonyl polyphosphite complex of rhodium with mixed organophosphorus ligands.
  • the complex having the general formula HRh(CO)(A)(B), where A is a polyphosphite ligand and B is an organophosphine or an organophosphinite.
  • W09819990 is mainly about avoiding catalyst deactivation by adding some acid to the hydroformylation process, but it also teaches that in order to further improve the stability of the catalyst system it is preferred to add some organophosphorus compound, e.g. monodentate phosphine.
  • phosphine compound is coordinating to the rhodium phosphite ligand complex.
  • a rhodium ligand complex comprising both phosphite and phosphine however has a much poorer product selectivity than a rhodium ligand complex comprising only phosphite. It is therefore desirable to find a way to avoid the organophosphite ligand oxidation without decreasing the product selectivity.
  • the present invention accordingly refers to a carbonylation process, such as hydroformylation, catalysed by one or more Group VIII transition metal(s) wherein said Group VIII transition metal is complexed with at least one phosphite ligand of Formula (I) and in the presence of an anti-oxidant selected from the group consisting of tertiary phosphines, such as triarylphosphines, dicycloalkylarylphosphines and/or cycloalkyldiarylphosphines.
  • tertiary phosphines such as triarylphosphines, dicycloalkylarylphosphines and/or cycloalkyldiarylphosphines.
  • phosphine anti-oxidants include, in embodiments of the present invention, phenyldi(o-, m- or /?-tolyl)phosphines, diphenyl(o-, m- or /?-tolyl)phosphines, tri(o-, m- or /?-tolyl)phosphines, phenyldibenyzylphosphines, diphenylbenzylphosphines, tribenzylphosphines, phenyldinaphthyl- phosphines, diphenylnaphthylphosphines, trinaphthylphosphines, dicyclohexylbenzylphosphines and/or cyclohexyldibenzylphosphines.
  • Said Formula (I) ligand is suitably used in an amount of 0.5-15, such as 1-10 or 1-5, % by weight calculated on total reaction mixture and said anti-oxidant in an amount of 0.01-5, such as 0.05-2, % likewise by weight calculated on total hydroformylation mixture, corresponding to a Group VIII transition metakphosphite ligand of Formula (I): anti-oxidant molar ratio of 1:2:0.3-0.9.
  • a monophosphine protects the phosphite ligand from oxidation due to air ingress.
  • One purpose of the present invention is to ensure ligand stability during storage. However in air-free process environments, like in most hydroformylation reactors, the presence of phosphine is not needed, or in only very small amounts. On the contrary there is a risk that the presence of phosphine has a negative effect on the product selectivity since the phosphine compete with the phosphite ligand on coordinating to the Group VIII transition metal, usually rhodium.
  • One embodiment of the present invention refers to catalyst preparation. Due to the oxygen scavenging property of the phosphine it is possible to prepare the catalyst solution without the phosphite ligand being oxidized due to air ingress. Catalyst preparation in air-free conditions are more expensive. The monophosphine is added in sub stoichiometric amounts in order to avoid complexation and when the catalyst solution is added to the hydroformylation process there is almost no phosphine left, which is beneficial for the product selectivity.
  • -Ar is a group of Formula. (II) and -R , -R , - R 6 and -R 8 are n-butyl, z ' so-butyl or tert-buty ⁇ .
  • -R 4 and -R 5 are methyl and in yet a further preferred embodiments said group of Formula (II) or (III) is suitably substituted by at least one linear or branched Ci-C 6 alkyl group.
  • the process of the present invention is advantageously and preferably a hydroformylation of at least one C2-C12 olefin, such as ethylene, a propene, a butene, including 1-butene and cis- or trans- 2-butene, a pentene and/or a hexene, in presence of at least one Group VIII transition metal, such as ruthenium, palladium, osmium, iridium, platinum and rhodium, catalyst or catalyst precursor.
  • C2-C12 olefin such as ethylene, a propene, a butene, including 1-butene and cis- or trans- 2-butene, a pentene and/or a hexene
  • Group VIII transition metal such as ruthenium, palladium, osmium, iridium, platinum and rhodium, catalyst or catalyst precursor.
  • Said Group VIII transition metal is suitably and advantageously present in said process in an amount of 20-1000, such as 50-550, ppm by weight of obtained hydroformylation mixture.
  • said Group VIII transition metal catalyst is suitably and preferably charged in form of a precursor selected from the group consisting of a hydride, a halide, anitrate, a carbonyl compound, an acetate and a dicarbonyl-acetylacetonate.
  • said Group VIII transition metal is rhodium and said precursor is selected from rhodium(III)nitrate, rhodium(III)acetate, rhodium(I)acetate, acetyl- acetonatedicarbonyl rhodium(I), di(rhodium)tetracarbonyl dichloride, dodecancarbonyl- tetrarhodium and/or hexadecane carbonylhexarhodium.
  • the present invention refers to a ligand mixture comprising at least one phosphite ligand of Formula I and at least one anti-oxidant selected from the group consisting of tertiary phosphines, such as triarylphosphines, dicycloalkylarylphosphines and/or cycloalkyldiarylphosphines.
  • tertiary phosphines such as triarylphosphines, dicycloalkylarylphosphines and/or cycloalkyldiarylphosphines.
  • anti-oxidant phosphine ligands include, but is not limited to, phenyldi(o-, m- or /?-tolyl)phosphines, diphenyl(o-, m- or p- tolyl)phosphines, tri(o-, m- or /?-tolyl)phosphines, phenyldibenyzylphosphines, diphenylbenzyl- phosphines, tribenzylphosphines, phenyldinaphthylphosphines, diphenylnaphthylphosphines, trinaphthylphosphines, dicyclohexylbenzylphosphines and/or cyclohexyldibenzylphosphines.
  • Diphenyl(p-tolyl)phosphine was, as an anti-oxidant, mixed with a phosphite ligand of Formula (I) having CAS no. 198979-98-5, hereinafter designated A4N3, and added to sample vials containing valeric aldehyde.
  • the amounts of anti-oxidant investigated were 0% (blank sample), 0.25% and 2% by weight calculated on the total mixture and A4N3 amounts added were 2% by weight calculated on total mixture.
  • the test was repeated using tri(p-tolyl)phosphine (TPTP) and tri(o-tolyl)phosphine (TOTP) as anti-oxidants.
  • ligand A4N3 was added at 1.05% by weight on reaction mixture and diphenyl(p-tolyl)phosphine (DPTP), tri(p-tolyl)phosphine (TPTP) or tri(o- tolyl)phosphine (TOTP) were used as anti-oxidants added at 0.07% by weight on reaction mixture, corresponding to a Rh:A4N3: anti-oxidant molar ratio of 1:2:0.4-1.3.
  • Hydroformylation of butene was carried out at 95 °C and 14 bar pressure of a syngas, comprising CO and H 2 , for 5-7 hrs.
  • the reaction mixture was pumped via a piston pump through a React- IR, IR scans were recorded at 30 second intervals and samples were taken at regular intervals for GC/HPLC analysis.
  • the reactor was cooled, gasses vented to a dump vessel, the reactor was purged several times with N 2 and the reaction mixture was then removed via the sample point.
  • the products regioselectivity were analysed showing that addition of the anti-oxidant in sub stoichiometric amounts does not negatively affect the selectivity, however when the anti-oxidant is added in stoichiometric excess a decreased selectivity is observed. Obtained regioselectivities are given in Table 2 as the ratio between linear and branched aldehydes.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé de carbonylation comprenant la soumission d'au moins une oléfine à une hydroformylation en présence d'un gaz de synthèse, comprenant du monoxyde de carbone et de l'hydrogène, au moins un catalyseur de métal de transition du groupe VIII ou un précurseur de catalyseur et au moins un ligand de phosphite de formule (I) et au moins un anti-oxydant choisi dans le groupe constitué par des phosphines tertiaires, telles que les triarylphosphines, les dicycloalkylarylphosphines et/ou les cycloalkyldiarylphosphines. Selon un autre aspect, la présente invention concerne un mélange de ligands comprenant au moins un ligand de phosphite de formule (I) et au moins ledit antioxydant.
PCT/SE2018/050120 2017-02-09 2018-02-09 Procédé de carbonylation et composition de ligand comprenant un ligand de phosphite bidenté et un anti-oxydant de phosphine tertiaire Ceased WO2018147793A1 (fr)

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CN201880011061.4A CN110267936A (zh) 2017-02-09 2018-02-09 羰基化方法以及包含双齿亚磷酸酯配体和叔膦抗氧化剂的配体组合物

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CN111138493A (zh) * 2020-01-13 2020-05-12 上海华谊（集团）公司 一种合成双亚磷酸酯的方法
CN115850041B (zh) * 2022-11-30 2024-03-01 上海簇睿低碳能源技术有限公司 一种烯烃氢甲酰化反应制备醛的方法、酚类抗氧化剂的用途和提高催化体系稳定性的方法
CN116237086B (zh) * 2023-03-23 2023-11-03 中国科学院长春应用化学研究所 基于抗氧化策略的乙烯羰基化制丙酸甲酯高效催化剂体系

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EP0839787A1 (fr) * 1996-11-04 1998-05-06 Dsm N.V. Procédé pour la préparation d'un aldéhyde
US5910600A (en) * 1996-04-30 1999-06-08 Mitsubishi Chemical Corporation Bisphosphite compound, process for its production and hydroformylation process employing the bisphosphite compound
US6610891B1 (en) * 1999-12-03 2003-08-26 Mitsubishi Chemical Corporation Method of producing aldehydes
WO2006098685A1 (fr) * 2005-03-16 2006-09-21 Perstorp Specialty Chemicals Ab Procede d'hydroformylation a isoselectivite amelioree
JP2008031053A (ja) * 2006-07-26 2008-02-14 Mitsubishi Chemicals Corp アリル化合物の異性化方法
WO2010117391A1 (fr) * 2009-03-31 2010-10-14 Dow Technology Investment Llc Procede d'hydroformylation avec un ligand bisphosphite a double extremite ouverte
RU2584952C1 (ru) * 2015-03-26 2016-05-20 Общество с ограниченной ответственностью "Объединенный центр исследований и разработок" (ООО "РН-ЦИР") Гидрид-карбонильный полифосфитный комплекс родия со смешанными фосфорорганическими лигандами для катализа процесса гидроформилирования олефинов

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JP2000103797A (ja) * 1998-09-29 2000-04-11 Mitsubishi Chemicals Corp ロジウム−（二座キレート配位子）二核錯体
CN1986055B (zh) * 2006-12-22 2012-06-27 中国科学院上海有机化学研究所 一种丙烯氢甲酰化催化体系和方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5910600A (en) * 1996-04-30 1999-06-08 Mitsubishi Chemical Corporation Bisphosphite compound, process for its production and hydroformylation process employing the bisphosphite compound
EP0839787A1 (fr) * 1996-11-04 1998-05-06 Dsm N.V. Procédé pour la préparation d'un aldéhyde
US6610891B1 (en) * 1999-12-03 2003-08-26 Mitsubishi Chemical Corporation Method of producing aldehydes
WO2006098685A1 (fr) * 2005-03-16 2006-09-21 Perstorp Specialty Chemicals Ab Procede d'hydroformylation a isoselectivite amelioree
JP2008031053A (ja) * 2006-07-26 2008-02-14 Mitsubishi Chemicals Corp アリル化合物の異性化方法
WO2010117391A1 (fr) * 2009-03-31 2010-10-14 Dow Technology Investment Llc Procede d'hydroformylation avec un ligand bisphosphite a double extremite ouverte
RU2584952C1 (ru) * 2015-03-26 2016-05-20 Общество с ограниченной ответственностью "Объединенный центр исследований и разработок" (ООО "РН-ЦИР") Гидрид-карбонильный полифосфитный комплекс родия со смешанными фосфорорганическими лигандами для катализа процесса гидроформилирования олефинов

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SE1730036A1 (en) 2018-08-10

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