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公开(公告)号：US10745336B2
公开(公告)日：2020-08-18
申请号：US16621123
申请日：2018-04-24
摘要： Disclosed are processes for making cyclohexanone from a feed mixture comprising cyclohexylbenzene, cyclohexanone, phenol, 3-cylclohexenone and optionally 2-cyclohexenone, comprising feeding the feed mixture to a first distillation column and hydrogenating a fraction from the first distillation column in a hydrogenation reactor separate from the first distillation in the presence of a hydrogenation catalyst under hydrogenation conditions. A cyclohexanone-rich upper effluent comprising 3-cyclohexenone and 2-cyclohexenone at low concentrations can be obtained from the first distillation column.
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公开(公告)号：US10351506B2
公开(公告)日：2019-07-16
申请号：US16072032
申请日：2017-04-11
IPC分类号： C07C67/54 , C07C51/265 , C07C67/02 , C07C67/03 , C07C67/08 , C07C63/331 , C07C69/76 , C08K5/12
摘要： This disclosure relates to methods for producing purified aromatic esters useful as plasticizers, to the purified aromatic esters, and to polymer compositions containing the purified esters. The purified aromatic esters can be produced by esterifying carboxylic acid with methyl or ethyl alcohol, separating the resulting methyl or ethyl esters from the carboxylic acid and any byproduct impurities, and then transesterifying the methyl or ethyl esters with C4 to C14 alcohol to produce the purified aromatic esters. Additionally, precipitation, filtration, and wash steps can be employed to purify the carboxylic acid, the methyl or ethyl alcohol, and/or the aromatic esters.
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公开(公告)号：US10053408B2
公开(公告)日：2018-08-21
申请号：US15504217
申请日：2015-08-03
发明人： Keith H. Kuechler , Jörg F. W. Weber , Ashley J. Poucher , Jason D. Davis , Christopher L. Becker , Jihad M. Dakka
CPC分类号： C07C45/006 , C07C7/005 , C07C7/04 , C07C7/12 , C07C37/74 , C07C37/82 , C07C45/79 , C07C45/82 , C07C2601/14 , Y02P20/52 , C07C49/403 , C07C39/04 , C07C13/28
摘要： Disclosed are processes for making cyclohexanone from a mixture comprising phenol, cyclohexanone, cyclohexylbenzene, and an S-containing component, comprising a step of removing at least a portion of the S-containing component to reduce poisoning of a hydrogenation catalyst used for hydrogenating phenol to cyclohexanone.
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公开(公告)号：US10752570B2
公开(公告)日：2020-08-25
申请号：US16621053
申请日：2018-04-24
摘要： Disclosed are processes for abating 3-cyclohexenone from a feed mixture comprising cyclohexylbenzene, cyclohexanone, phenol, and 3-cyclohexenone and cyclohexanone, comprising feeding the feed mixture to a first distillation column and a hydrogenating a fraction from in the presence of a hydrogenation catalyst under hydrogenation conditions. Hydrogenation can be carried out in a hydrogenation reactor separate from the first distillation column or in a hydrogenation zone disposed inside the first distillation column.
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公开(公告)号：US11161812B2
公开(公告)日：2021-11-02
申请号：US16096091
申请日：2017-04-18
发明人： Jörg F. W. Weber , Helge Jaensch , Andrew R. Witt , Christopher L. Becker , Kirk C. Nadler , Kendele S. Galvan , Amy B. Batton
IPC分类号： B01J19/00 , B01J19/18 , C07D209/48 , C07D307/89
摘要： Disclosed are novel processes for the production of cyclic imide compounds such as N-hydroxyphthalimide (NHPI). The processes may be particularly well-suited for commercial-scale production of cyclic imides such as NHPI. Such cyclic imide compounds are suitable for use as oxidation catalysts, and specifically may be used to oxidize cyclohexylbenzene to cyclohexyl-1-phenyl-1-hydroperoxide. Such an oxidation may be particularly useful in a process for the production of phenol and/or cyclohexanone from benzene via a process comprising hydroalkylation of benzene to cyclohexylbenzene, oxidation of the cyclohexylbenzene to cyclohexyl-1-phenyl-1-hydroperoxide, and cleavage of the cyclohexyl-1-phenyl-1-hydroperoxide to phenol and cyclohexanone. The cyclic imide production process may advantageously include water washing and reactant recovery steps to maximize purity and yield.
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公开(公告)号：US11014883B2
公开(公告)日：2021-05-25
申请号：US16096161
申请日：2017-04-18
发明人： Jörg F. W. Weber , Helge Jaensch , Andrew R. Witt , Christopher L. Becker , Kirk C. Nadler , Kendele S. Galvan , Amy B. Batton
IPC分类号： C07D209/48 , B01J31/02 , B01J37/04
摘要： Disclosed are novel processes for the production of cyclic imide compounds such as N-hydroxyphthalimide (NHPI). The processes may be particularly well-suited for commercial-scale production of cyclic imides such as NHPI. Such cyclic imide compounds are suitable for use as oxidation catalysts, and specifically may be used to oxidize cyclohexylbenzene to cyclohexyl-1-phenyl-1-hydroperoxide. Such an oxidation may be particularly useful in a process for the production of phenol and/or cyclohexanone from benzene via a process comprising hydroalkylation of benzene to cyclohexylbenzene, oxidation of the cyclohexylbenzene to cyclohexyl-1-phenyl-1-hydroperoxide, and cleavage of the cyclohexyl-1-phenyl-1-hydroperoxide to phenol and cyclohexanone. The cyclic imide production process may advantageously include water washing and reactant recovery steps to maximize purity and yield.
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公开(公告)号：US10252968B2
公开(公告)日：2019-04-09
申请号：US15742910
申请日：2016-06-17
发明人： Jihad M. Dakka , Ashley J. Malik , Christopher L. Becker , Jason D. Davis , Kirk C. Nadler , Jose M. Vargas , Tan-Jen Chen , Seth M. Washburn , Jörg F. W. Weber
摘要： Disclosed are novel processes for making cyclohexanone compositions, from a mixture comprising phenol, cyclohexanone, and cyclohexylbenzene. The process includes hydrogenation of a feed stream comprising phenol, cyclohexanone, and cyclohexylbenzene. The feed stream may be subjected to one or more pre-hydrogenation treatments, such as passing through one or more sorbents, addition of basic chemical agents, and/or addition of water, so as to improve catalyst activity, minimize undesired side reactions, and/or remove catalyst poisons from the feed stream. The feed stream may be provided to a hydrogenation reaction zone in the vapor phase, with periodic alterations to hydrogenation reaction conditions such that the feed is provided in mixed liquid and vapor phase in order to carry out liquid washing of a hydrogenation catalyst bed within the hydrogenation reaction zone.
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公开(公告)号：US10941099B2
公开(公告)日：2021-03-09
申请号：US16621035
申请日：2018-04-24
IPC分类号： C07C45/62 , C07C45/00 , C07C49/403
摘要： Disclosed are a process for abating 3-cyclohexenone from a feed mixture comprising 3-cylclohexenone and cyclohexanone, comprising a hydrogenation step of contacting the feed mixture with hydrogen in the presence of a hydrogenation catalyst under hydrogenation conditions to obtain a hydrogenated mixture, cyclohexanone-containing products comprising 3-cyclohexenone and/or 2-cyclohexenone at low concentrations, and compositions of matter useful for making such cyclohexanone-containing products, particularly by using such processes.
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公开(公告)号：US10570079B2
公开(公告)日：2020-02-25
申请号：US16280668
申请日：2019-02-20
摘要： Disclosed are processes for making such cyclohexanone compositions from a mixture comprising phenol, cyclohexanone, and cyclohexylbenzene. Such cyclohexanone compositions comprise at least 99 wt % cyclohexanone, at most 0.15 wt % water, and at most 500 wppm combined of certain cyclohexanone impurities selected from the group consisting of: benzene, cyclohexene, pentanal, cyclopentanol, cyclohexanol, and phenol.
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公开(公告)号：US10294178B2
公开(公告)日：2019-05-21
申请号：US15551839
申请日：2016-01-15
IPC分类号： C07C7/08 , C07C7/04 , C07C7/12 , C07C37/80 , C07C37/82 , C07C39/04 , C07C45/79 , C07C45/82 , C07C45/83 , C07C49/403
摘要： In a process for separating a mixture comprising cyclohexanone and phenol, a solid-phase basic material, such as basic ion-exchange resin, is used to remove acid and/or sulfur from the mixture prior to separation. The process results in reduced amount of contamination such as cyclic ethers in the cyclohexanone and/or phenol products.
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