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公开(公告)号:US10266469B2
公开(公告)日:2019-04-23
申请号:US16079155
申请日:2017-02-16
Applicant: BASF Agro B.V.
Inventor: Bernd Wolf , Michael Rack , Stefan Benson , Roland Goetz , Helmut Kraus
IPC: C07C35/18 , C07C29/17 , C07D303/04 , C07C35/00
Abstract: The present invention relates to a process for preparing terpinene-4-ol from limonene-4-ol via a hydrogenation reaction in the presence of a nickel catalyst.
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2.
公开(公告)号:US11384093B2
公开(公告)日:2022-07-12
申请号:US16498625
申请日:2018-03-23
Applicant: BASF Agro B.V.
Inventor: Stefan Benson , Michael Rack , Christiane Alznauer , Roland Goetz , Bernd Wolf
IPC: C07D493/08 , A01N25/02 , A01N43/90
Abstract: This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-iso-propyl-7-oxabicyclo[2.2.1]heptane of the formula (I) any of its individual enantiomers or any non-racemic mixture thereof, comprising the step of reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II) any of its individual enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (III) wherein X is a leaving group, in the presence of at least one base, at least one catalyst selected from rubidium salts, cesium salts and any combination thereof and at least one inert organic solvent S1.
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3.
公开(公告)号:US11897895B2
公开(公告)日:2024-02-13
申请号:US16770969
申请日:2018-12-06
Applicant: BASF AGRO B.V.
Inventor: Michael Rack , Stefan Benson , Bernd Wolf , Roland Goetz
IPC: C07D493/18
CPC classification number: C07D493/18
Abstract: This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I), any one of its individual enantiomers or any non-racemic mixture thereof any one of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of (a) reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II), any one of its individual enantiomers or any non-racemic mixture thereof (as defined in the description) with elemental sodium to form a sodium salt of the formula (III), any one of its individual enantiomers or any non-racemic mixture thereof (as defined in the description), and (b) reacting said sodium salt (III) with a 2-Methylbenzyl compound of the formula (IV) wherein X is a leaving group, wherein the steps (a) and (b) are conducted in the presence of at least one substantially anhydrous inert organic solvent.
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4.
公开(公告)号:US10710969B2
公开(公告)日:2020-07-14
申请号:US16334152
申请日:2017-09-07
Applicant: BASF Agro B.V.
Inventor: Stefan Benson , Michael Rack , Bernd Wolf , Roland Goetz , Joachim Gebhardt , Helmut Kraus
IPC: C07D307/00
Abstract: This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I) any of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of (a) reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II) any of its individual enantiomers or any non-racemic mixture thereof with a 2-Methylbenzyl compound of the formula (III) wherein X is a leaving group in the presence of at least one base capable of forming water or a C1-C4 alkyl alcohol under the reaction conditions, and at least one inert organic solvent, and (b) simultaneously removing water, the C1-C4 alkyl alcohol or any mixture thereof from the reaction mixture.
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公开(公告)号:US10538470B2
公开(公告)日:2020-01-21
申请号:US15571987
申请日:2016-04-22
Applicant: BASF Agro B.V.
Inventor: Bernd Wolf , Michael Rack , Stefan Benson , Helmut Kraus , Roland Goetz , Sukunath Narayanan , Chidambaram Rishinaradamangalam
IPC: C07D307/00 , C07C29/56 , C07C29/17 , C07D493/08
Abstract: The present invention relates to a process for the preparation of limonene-4-ol by an epoxide ring opening isomerization of terpinolene epoxide.
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公开(公告)号:US11072593B2
公开(公告)日:2021-07-27
申请号:US16309478
申请日:2017-06-01
Applicant: BASF Agro B.V.
Inventor: Joachim Gebhardt , Michael Rack , Bernd Wolf , Stefan Benson , Roland Goetz , Helmut Kraus
IPC: C07D301/16 , C07D303/04 , C07D493/08 , B01J19/00
Abstract: This invention relates to a process for the epoxidation of a tetrasubstituted alkene such as terpinolene to the corresponding epoxide such as terpinolene epoxide by reacting the tetrasubstituted alkene with performic acid prepared in situ from formic acid and hydrogen peroxide in the presence of at least one buffering agent. Further, the invention relates to the use of an oxidizing agent comprising hydrogen peroxide and formic acid for the in-situ epoxidation of a tetrasubstituted alkene.
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7.
公开(公告)号:US20210163496A1
公开(公告)日:2021-06-03
申请号:US16770969
申请日:2018-12-06
Applicant: BASF AGRO B.V.
Inventor: Michael Rack , Stefan Benson , Bernd Wolf , Roland Goetz
IPC: C07D493/18
Abstract: This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I), any one of its individual enantiomers or any non-racemic mixture thereof any one of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of (a) reacting (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (II), any one of its individual enantiomers or any non-racemic mixture thereof (as defined in the description) with elemental sodium to form a sodium salt of the formula (III), any one of its individual enantiomers or any non-racemic mixture thereof (as defined in the description), and (b) reacting said sodium salt (III) with a 2-Methylbenzyl compound of the formula (IV) wherein X is a leaving group, wherein the steps (a) and (b) are conducted in the presence of at least one substantially anhydrous inert organic solvent.
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公开(公告)号:US10344008B2
公开(公告)日:2019-07-09
申请号:US15571627
申请日:2016-04-28
Applicant: BASF AGRO B.V.
Inventor: Bernd Wolf , Michael Rack , Stefan Benson , Helmut Kraus , Roland Goetz , Sukunath Narayanan , Chidambaram Rishinaradamangalam
IPC: C07D301/12 , C07C29/17 , C07C29/56 , C07C35/18 , C07D303/04 , C07D493/08
Abstract: The present invention relates to a process for the preparation of terpinolene epoxide by epoxidation of terpinolene.
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公开(公告)号:US10266468B2
公开(公告)日:2019-04-23
申请号:US16079152
申请日:2017-02-16
Applicant: BASF Agro B.V.
Inventor: Bernd Wolf , Michael Rack , Stefan Benson , Roland Goetz , Helmut Kraus
IPC: C07C35/18 , C07C29/17 , C07C303/04 , C07C29/132 , C07C29/56 , B01J25/02
Abstract: The present invention relates to a process for preparing a mixture of terpene alcohols comprising limonene-4-ol and terpinene-4-ol from terpinolene epoxide via an isomerization and/or hydrogenation reaction in the presence of a copper catalyst.
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