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公开(公告)号:US10294191B2
公开(公告)日:2019-05-21
申请号:US15213449
申请日:2016-07-19
申请人: EVONIK DEGUSSA GMBH
发明人: Kaiwu Dong , Ralf Jackstell , Matthias Beller , Robert Franke , Dieter Hess , Katrin Marie Dyballa , Dirk Fridag , Frank Geilen
IPC分类号: C07F15/00 , C07F9/28 , B01J27/185 , C07C67/38 , C07F9/58 , C07F9/572 , C07F9/6506 , B01J31/24 , B01J31/22 , C07F9/655 , C07F9/6553 , C07F17/02
摘要: The invention relates to compounds of formula (I) where R1 is selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl; R2 is selected from —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, —(C3-C20)-heteroaryl; R3 is —(C3-C20)-heteroaryl; and R1, R2 and R3 may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl, —O—(C1-C12)-alkyl-(C6-C20)-aryl, —O—(C3-C12)-cycloalkyl, —S—(C1-C12)-alkyl, —S—(C3-C12)-cycloalkyl, —COO—(C1-C12)-alkyl, —COO—(C3-C12)-cycloalkyl, —CONH—(C1-C12)-alkyl, —CONH—(C3-C12)-cycloalkyl, —CO—(C1-C12)-alkyl, —COO—(C3-C12)-cycloalkyl, —N—[(C1-C12)-alkyl]2, —(C6-C20)-aryl, —(C6-C20)-aryl-(C1-C12)-alkyl, —(C6-C20)-aryl-O—(C1-C12)-alkyl, —(C3-C20)-heteroaryl, —(C3-C20)-heteroaryl-(C1-C12)-alkyl, —(C3-C20)-heteroaryl-O—(C1-C12)-alkyl, —COOH, —OH, —SO3H, —NH2, halogen. The invention further relates to Pd complexes comprising the compound according to the invention and to the use thereof in alkoxycarbonylation.
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公开(公告)号:US10227278B2
公开(公告)日:2019-03-12
申请号:US15773613
申请日:2016-08-02
申请人: Evonik Degussa GmbH
发明人: Katrin Marie Dyballa , Robert Franke , Dirk Fridag , Markus Schwarz , Hermann-Josef Schulte-Althoff , Frank Geilen
摘要: The production of 2-propylheptanol described here is effected via Rh-catalyzed hydroformylation of C4-olefin to afford C5-aldehyde, aldol condensation to afford the C10-aldehyde and hydrogenation to afford the C10-alcohol. The emphasis is on the hydroformylation and the ligand employed therein. The problem addressed by the invention is that of reducing the costs of 2PH production. This problem is solved when a cheaper catalyst system which simultaneously achieves a better regioselectivity is employed in the hydroformylation. This catalyst system contains rhodium as the central atom and is complexed with the ligand (1):
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公开(公告)号:US10202329B2
公开(公告)日:2019-02-12
申请号:US15213453
申请日:2016-07-19
申请人: EVONIK DEGUSSA GMBH
发明人: Kaiwu Dong , Helfried Neumann , Ralf Jackstell , Matthias Beller , Robert Franke , Dieter Hess , Katrin Marie Dyballa , Dirk Fridag , Frank Geilen
IPC分类号: C07F9/58 , C07C67/38 , C07F9/572 , C07F9/6506 , C07F15/00 , B01J31/24 , B01J31/22 , C07F9/655 , C07F9/6553 , C07F17/02
摘要: The invention relates to a compound of formula (I) where R1 and R3 are each a heteroaryl radical having five ring atoms, R2 and R4 are each independently selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl; R1 and R3 may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl, —O—(C1-C12)-alkyl-(C6-C20)-aryl, —O—(C3-C12)-cycloalkyl, —S—(C1-C12)-alkyl, —S—(C3-C12)-cycloalkyl, —COO—(C1-C12)-alkyl, —COO—(C3-C12)-cycloalkyl, —CONH—(C1-C12)-alkyl, —CONH—(C3-C12)-cycloalkyl, —CO—(C1-C12)-alkyl, —CO—(C3-C12)-cycloalkyl, —N—[(C1-C12)-alkyl]2, —(C6-C20)-aryl, —(C6-C20)-aryl-(C1-C12)-alkyl, —(C6-C20)-aryl-O—(C1-C12)-alkyl, —(C3-C20)-heteroaryl, —(C3-C20)-heteroaryl-(C1-C12)-alkyl, —(C3-C20)-heteroaryl-O—(C1-C12)-alkyl, —COOH, —OH, —SO3H, —NH2, halogen; and R2 and R4, if they are —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl or —(C6-C20)-aryl, may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl, —O—(C1-C12)-alkyl-(C6-C20)-aryl, —O—(C3-C12)-cycloalkyl, —S—(C1-C12)-alkyl, —S—(C3-C12)-cycloalkyl, —COO—(C1-C12)-alkyl, —COO—(C3-C12)-cycloalkyl, —CONH—(C1-C12)-alkyl, —CONH—(C3-C12)-cycloalkyl, —CO—(C1-C12)-alkyl, —CO—(C3-C12)-cycloalkyl, —N—[(C1-C12)-alkyl]2, —(C6-C20)-aryl, —(C6-C20)-aryl-(C1-C12)-alkyl, —(C6-C20)-aryl-O—(C1-C12)-alkyl, —(C3-C20)-heteroaryl, —(C3-C20)-heteroaryl-(C1-C12)-alkyl, —(C3-C20)-heteroaryl-O—(C1-C12)-alkyl, —COOH, —OH, —SO3H, —NH2, halogen; excluding the compounds of the formulae (1) and (2) The invention further relates to precursors for preparation of the compound according to the invention, to Pd complexes comprising the compound according to the invention and to the use thereof in alkoxycarbonylation.
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公开(公告)号:US10155200B2
公开(公告)日:2018-12-18
申请号:US15040058
申请日:2016-02-10
申请人: Evonik Degussa GmbH
发明人: Frank Geilen , Robert Franke , Bart Hamers
摘要: The invention deals with the separation of homogeneous catalysts from reaction mixtures with the help of organophilic nanofiltration. It is based on the object of indicating an option as to how organophilic nanofiltration can be used economically for separating off homogeneous catalysts from reaction mixtures if the separation-active material of the membrane satisfying the separation aim is not available in sufficiently large amounts or only at high cost. This object is achieved by taking into consideration a particular membrane performance indicator during the design and/or the execution of the corresponding membrane separation process.
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公开(公告)号:US10000440B2
公开(公告)日:2018-06-19
申请号:US15356507
申请日:2016-11-18
申请人: Evonik Degussa GmbH
发明人: Helene Reeker , Guido Stochniol , Dietrich Maschmeyer , Horst-Werner Zanthoff , Jörg Schallenberg , Frank Geilen , Katrin Marie Dyballa , Dirk Fridag , Stephan Peitz , Lena Altmann , Robert Franke
IPC分类号: C07C67/08 , C07C2/24 , C07C29/141 , C07C45/50
CPC分类号: C07C67/08 , C07C2/24 , C07C29/141 , C07C45/50 , C07C45/505 , C07C2521/12 , C07C2523/755 , Y02P20/52 , C07C47/02 , C07C31/125 , C07C69/80 , C07C11/02
摘要: The invention relates to a process for preparing an ester mixture, in which an n-butene-containing feed mixture having a composition which changes over time is first oligomerized and then converted by hydroformylation, hydrogenation and esterification to an ester mixture. In this process, an approximation of the actual viscosity of the ester mixture is determined. The problem that it addresses is that of specifying a comparatively simple process which enables conversion of an n-butene with a variable composition over time to an ester mixture having a viscosity which can be kept very substantially constant over a long period even when an inconstant C4 source which delivers fluctuating qualities over this period is utilized. This is achieved through controlled use of a second raw material, namely ethene. It has been found that the viscosity of n-butene-based ester mixtures can be influenced by controlled use of ethene in the preparation of the ester precursors. Specifically, the invention proposes two measures by which the ethene can be used: either directly as C2 olefin or as C8 olefin after prior separate oligomerization.
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公开(公告)号:US10544174B2
公开(公告)日:2020-01-28
申请号:US15649743
申请日:2017-07-14
申请人: EVONIK DEGUSSA GMBH
发明人: Kaiwu Dong , Ralph Jackstell , Matthias Beller , Dirk Fridag , Dieter Hess , Katrin Marie Dyballa , Frank Geilen , Robert Franke
IPC分类号: C07F9/50 , C07C67/38 , C07F15/00 , C07D403/14 , C07D405/14
摘要: The invention relates to a process comprising the following process steps: a) introducing an ethylenically unsaturated compound; b) adding a monophosphine ligand and a compound which comprises Pd, or adding a complex comprising Pd and a monophosphine ligand; c) adding an aliphatic alcohol; d) supplying CO; e) heating the reaction mixture, the ethylenically unsaturated compound being reacted to form an ester; where the monophosphine ligand is a compound of formula (I) where R1 is selected from —(C1-C12)-alkyl, —O—(C1-C12)-alkyl, —O—(C6-C20)-aryl, —(C6-C20)-aryl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C3-C20)-heteroaryl; R2 is selected from —(C6-C20)-aryl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C3-C20)-heteroaryl; R3 is —(C3-C20)-heteroaryl; and R1, R2 and R3 may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl, —O—(C1-C12)-alkyl-(C6-C20)-aryl, —O—(C3-C12)-cycloalkyl, —S—(C1-C12)-alkyl, —S—(C3-C12)-cycloalkyl, —COO—(C1-C12)-alkyl, —COO—(C3-C12)-cycloalkyl, —CONH—(C1-C12)-alkyl, —CONH—(C3-C12)-cycloalkyl, —CO—(C1-C12)-alkyl, —CO—(C3-C12)-cycloalkyl, —N—[(C1-C12)-alkyl]2, —(C6-C20)-aryl, —(C6-C20)-aryl-(C1-C12)-alkyl, —(C6-C20)-aryl-O—(C1-C12)-alkyl, —(C3-C20)-heteroaryl, —(C3-C20)-heteroaryl-(C1-C12)-alkyl, —(C3-C20)-heteroaryl-O—(C1-C12)-alkyl, —COOH, —OH, —SO3H, —NH2, halogen.
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公开(公告)号:US10202409B2
公开(公告)日:2019-02-12
申请号:US15649781
申请日:2017-07-14
申请人: EVONIK DEGUSSA GMBH
发明人: Kaiwu Dong , Ralf Jackstell , Helfried Neumann , Matthias Beller , Dirk Fridag , Dieter Hess , Katrin Marie Dyballa , Frank Geilen , Robert Franke
IPC分类号: C07F17/02 , C07C67/38 , C07F15/00 , C07C213/02
摘要: Compound of formula (I) where R2, R4 are each independently selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl; the R1, R3 radicals are each a —(C3-C20)-heteroaryl radical; R1, R3 may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl, —O—(C1-C12)-alkyl-(C6-C20)-aryl, —O—(C3-C12)-cycloalkyl, —S—(C1-C12)-alkyl, —S—(C3-C12)-cycloalkyl, —COO—(C1-C12)-alkyl, —COO—(C3-C12)-cycloalkyl, —CONH—(C1-C12)-alkyl, —CONH—(C3-C12)-cycloalkyl, —CO—(C1-C12)-alkyl, —CO—(C3-C12)-cycloalkyl, —N—[(C1-C12)-alkyl]2, —(C6-C20)-aryl, —(C6-C20)-aryl-(C1-C12)-alkyl, —(C6-C20)-aryl-O—(C1-C12)-alkyl, —(C3-C20)-heteroaryl, —(C3-C20)-heteroaryl-(C1-C12)-alkyl, —(C3-C20)-heteroaryl-O—(C1-C12)-alkyl, —COOH, —OH, —SO3H, —NH2, halogen; R2, R4, if they are —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl or —(C6-C20)-aryl, may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl, —O—(C1-C12)-alkyl-(C6-C20)-aryl, —O—(C3-C12)-cycloalkyl, —S—(C1-C12)-alkyl, —S—(C3-C12)-cycloalkyl, —COO—(C1-C12)-alkyl, —COO—(C3-C12)-cycloalkyl, —CONH—(C1-C12)-alkyl, —CONH—(C3-C12)-cycloalkyl, —CO—(C1-C12)-alkyl, —CO—(C3-C12)-cycloalkyl, —N—[(C1-C12)-alkyl]2, —(C6-C20)-aryl, —(C6-C20)-aryl-(C1-C12)-alkyl, —(C6-C20)-aryl-O—(C1-C12)-alkyl, —(C3-C20)-heteroaryl, —(C3-C20)-heteroaryl-(C1-C12)-alkyl, —(C3-C20)-heteroaryl-O—(C1-C12)-alkyl, —COOH, —OH, —SO3H, —NH2, halogen. The invention also relates to Pd complexes of the compound according to the invention, and to the use thereof in an alkoxycarbonylation process.
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公开(公告)号:US10077228B2
公开(公告)日:2018-09-18
申请号:US15213456
申请日:2016-07-19
申请人: EVONIK DEGUSSA GMBH
发明人: Kaiwu Dong , Helfried Neumann , Ralf Jackstell , Matthias Beller , Robert Franke , Dieter Hess , Katrin Marie Dyballa , Dirk Fridag , Frank Geilen
IPC分类号: C07C67/38 , C07F9/58 , C07F9/6506 , C07F15/00 , B01J31/24 , B01J31/22 , C07F9/572 , C07F9/655 , C07F9/6553 , C07F17/02
CPC分类号: C07C67/38 , B01J31/2295 , B01J31/24 , B01J31/2404 , B01J31/2409 , B01J2231/321 , B01J2231/49 , B01J2531/0208 , B01J2531/824 , B01J2531/842 , C07F9/572 , C07F9/58 , C07F9/6506 , C07F9/65515 , C07F9/655345 , C07F15/006 , C07F17/02 , C07C69/24
摘要: The invention relates to a compound of formula (I) where R1, R2, R3, R4 are each independently selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, —(C3-C20)-heteroaryl; at least one of the R1, R2, R3, R4 radicals is a —(C6-C20)-heteroaryl radical having at least six ring atoms; and R1, R2, R3, R4, if they are —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, —(C3-C20)-heteroaryl or —(C6-C20)-heteroaryl, may each independently be substituted by one or more substituents selected from —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —O—(C1-C12)-alkyl, —O—(C1-C12)-alkyl-(C6-C20)-aryl, —O—(C3-C12)-cycloalkyl, —S—(C1-C12)-alkyl, —S—(C3-C12)-cycloalkyl, —COO—(C1-C12)-alkyl, —COO—(C3-C12)-cycloalkyl, —CONH—(C1-C12)-alkyl, —CONH—(C3-C12)-cycloalkyl, —CO—(C1-C12)-alkyl, —CO—(C3-C12)-cycloalkyl, —N—[(C1-C12)-alkyl]2, —(C6-C20)-aryl, —(C6-C20)-aryl-(C1-C12)-alkyl, —(C6-C20)-aryl-O—(C1-C12)-alkyl, —(C3-C20)-heteroaryl, —(C3-C20)-heteroaryl-(C1-C12)-alkyl, —(C3-C20)-heteroaryl-O—(C1-C12)-alkyl, —COOH, —OH, —SO3H, —NH2, halogen. The invention further relates to precursors for preparation of the compound according to the invention, to Pd complexes comprising the compound according to the invention and to the use thereof in alkoxycarbonylation.
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公开(公告)号:US09963644B2
公开(公告)日:2018-05-08
申请号:US15103805
申请日:2014-11-05
申请人: Evonik Degussa GmbH
发明人: Frank Geilen , Stephan Peitz , Guido Stochniol , Markus Winterberg , Dietrich Maschmeyer , Armin Rix , Mathias Vogt
IPC分类号: C10G25/00 , C07C7/12 , C07C7/13 , C10G25/05 , C10G53/08 , C10G55/04 , C10G57/00 , C10G57/02 , C10G67/06 , B01J20/06 , B01J20/08 , B01J20/28 , C10G53/14 , B01J23/80 , B01J35/00
CPC分类号: C10G25/003 , B01J20/06 , B01J20/08 , B01J20/2803 , B01J23/80 , B01J35/0053 , B01J2220/42 , C07C7/13 , C10G25/05 , C10G53/08 , C10G53/14 , C10G55/04 , C10G57/00 , C10G57/005 , C10G57/02 , C10G67/06 , C10G2300/202 , C07C11/08
摘要: The invention relates to a method for cleaning hydrocarbon mixtures, in which a contaminated hydrocarbon mixture comprising hydrocarbons having three to eight carbon atoms is at least partly freed of impurities by contacting with a solid sorbent, wherein the hydrocarbon mixture is exclusively in the liquid state during contact with the sorbent. The object of the invention is to specify a process for cleaning liquid C3 to C8 hydrocarbon mixtures, which is based on a readily available but non-carcinogenic sorbent and which achieves better purities compared to traditional molecular sieves. This object is achieved by using, as sorbents, solid materials of the following composition: copper oxide: 10% to 60% by weight (calculated as CuO); zinc oxide: 10% to 60% by weight (calculated as ZnO); aluminum oxide: 10% to 30% by weight (calculated as Al2O3); other substances: 0% to 5% by weight. Materials of this kind are otherwise used as catalysts in methanol synthesis.
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公开(公告)号:US09908910B2
公开(公告)日:2018-03-06
申请号:US15381722
申请日:2016-12-16
申请人: EVONIK DEGUSSA GMBH
发明人: Katrin Marie Dyballa , Robert Franke , Dirk Fridag , Dieter Hess , Frank Geilen , Galina Morales Torres , Detlef Selent , Armin Börner
IPC分类号: C07C45/50 , C07F15/00 , C07F9/6571 , C07F9/6509
CPC分类号: C07F15/008 , C07C45/505 , C07F9/650952 , C07F9/657154
摘要: The invention relates to Rh, Ru, Co and Ir complexes comprising bidentate diphosphoramidites as ligands and to the use thereof as catalysts for the hydroformylation of olefins. The invention also relates to a process for preparing an aldehyde from an olefin using the complexes or ligands mentioned.
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