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1.
公开(公告)号:US10519090B2
公开(公告)日:2019-12-31
申请号:US16216053
申请日:2018-12-11
申请人: EVONIK DEGUSSA GMBH
发明人: Rui Sang , Peter Kucmierczyk , Kaiwu Dong , Ralf Jackstell , Matthias Beller , Robert Franke
摘要: Process for Pd-catalyzed hydroxycarbonylation of diisobutene:acetic acid/diisobutene ratio.
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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: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:US11028110B2
公开(公告)日:2021-06-08
申请号:US15649770
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: C07F9/50 , C07C67/36 , C07C67/38 , C07D471/00 , C07F15/00
摘要: The invention relates to a process comprising the following process steps: a) introducing a first alcohol, the first alcohol having 2 to 30 carbon atoms; b) adding a phosphine ligand and a compound which comprises Pd, or adding a complex comprising Pd and a phosphine ligand; c) adding a second alcohol; d) supplying CO; e) heating the reaction mixture, the first alcohol reacting with CO and the second alcohol to form an ester; where the phosphine ligand is a compound of formula (I) where m and n are each independently 0 or 1; 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 —(C3-C20)-heteroaryl radical; and R1, R2, R3, R4, if they are —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl or —(C3-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.
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公开(公告)号:US10696702B2
公开(公告)日:2020-06-30
申请号:US16269940
申请日:2019-02-07
申请人: EVONIK DEGUSSA GMBH
发明人: Jiawang Liu , Kaiwu Dong , Robert Franke , Helfried Neumann , Ralf Jackstell , Matthias Beller
摘要: Propyl-bridged diphosphine compounds, metal complexes of these compounds and the use thereof for alkoxycarbonylation.
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6.
公开(公告)号:US10562838B2
公开(公告)日:2020-02-18
申请号:US15651042
申请日:2017-07-17
申请人: EVONIK DEGUSSA GMBH
发明人: Xianjie Fang , Kaiwu Dong , Helfried Neumann , Ralf Jackstell , Matthias Beller , Dirk Fridag , Dieter Hess , Katrin Marie Dyballa , Frank Geilen , Robert Franke
摘要: Process comprising the following process steps: a) introducing an ethylenically unsaturated compound; b) adding a ligand-metal complex comprising Pd and a bidentate phosphine ligand, or adding a bidentate phosphine ligand and a compound which comprises Pd; c) adding an alcohol; d) supplying CO; e) heating the reaction mixture, the ethylenically unsaturated compound being reacted to form an ester, where the reaction mixture is admixed with less than 0.1 mol %, based on the amount of substance of the ethylenically unsaturated compound, of Brønsted acids having an acid strength of pKa≤3, characterized in that the phosphine ligand is substituted on at least one phosphorus atom by at least one heteroaryl radical.
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公开(公告)号:US10508071B2
公开(公告)日:2019-12-17
申请号:US16043644
申请日:2018-07-24
申请人: EVONIK DEGUSSA GMBH
发明人: Rui Sang , Jie Liu , Kaiwu Dong , Ralf Jackstell , Matthias Beller , Robert Franke
摘要: Process for methoxycarbonylation with formic acid and methanol.
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公开(公告)号:US10550060B2
公开(公告)日:2020-02-04
申请号:US16215991
申请日:2018-12-11
申请人: EVONIK DEGUSSA GMBH
发明人: Rui Sang , Peter Kucmierczyk , Kaiwu Dong , Ralf Jackstell , Matthias Beller , Robert Franke
摘要: Process for the direct conversion of alkenes to carboxylic acids.
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公开(公告)号:US10544079B2
公开(公告)日:2020-01-28
申请号:US16189029
申请日:2018-11-13
申请人: EVONIK DEGUSSA GMBH
发明人: Rui Sang , Peter Kucmierczyk , Kaiwu Dong , Ralf Jackstell , Matthias Beller , Robert Franke
摘要: Process for the direct conversion of diisobutene to a carboxylic acid.
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公开(公告)号:US10087134B2
公开(公告)日:2018-10-02
申请号:US15651062
申请日:2017-07-17
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
摘要: The invention relates to a process comprising the process steps of: a) initially charging an ether having from 3 to 30 carbon atoms; b) adding a phosphine ligand and a compound comprising Pd, or adding a comprising Pd and a phosphine ligand; c) feeding in CO; d) heating the reaction mixture, with conversion of the ether; wherein the phosphine ligand is a compound of formula (I) where m and n are each independently 0 or 1; 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 —(C3-C20)-heteroaryl radical; and R1, R2, R3, R4, if they are —(C1-C12)-alkyl, —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl or —(C3-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, —SO3H, —NH2, halogen; and wherein no alcohol is added to the reaction mixture.
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