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    Manufacture of α-tocopherol
    1.
    发明授权
    Manufacture of α-tocopherol 有权
    α-生育酚的制造

    公开(公告)号：US07626046B2

    公开(公告)日：2009-12-01

    申请号：US10494005

    申请日：2002-10-23

    申请人： Werner Bonrath ,  David Carl Burdick ,  Frank Schager ,  Dominik Thomas ,  Thomas Netscher

    发明人： Werner Bonrath ,  David Carl Burdick ,  Frank Schager ,  Dominik Thomas ,  Thomas Netscher

    IPC分类号： C07D311/72

    CPC分类号： C07D311/72

    摘要： A process for the manufacture of (all-rac)-α-tocopherol comprises submitting isolated, purified phytyltrimethylhydroquinone to acid catalysis, thereby promoting ring closure to (all-rac)-α-t-tocopherol. The process can be conducted in the absence or presence of an added solvent, and when a solvent or solvent mixture is used the solvent or at least one solvent component of the solvent mixture is preferably one with a dipole moment greater than 9×10−30 C-m (or 2.7D). The nature of the catalyst is immaterial, but the catalyst is preferably sulphuric acid, phosphoric acid, a polyperfluoroalkylenesulphonic acid, a “NH-acid”, a heteropoly acid, zinc chloride, boron trifluoride, aluminium trichloride, or a mixture of any f the aforementioned Brönsted acids with any of the aforementioned Lewis acids. The product of the process is the most active an industrially most important member of the vitamin E group.

    摘要翻译： 制备（全消旋）-α-生育酚的方法包括将分离的纯化的植酰三甲基氢醌提交到酸催化，从而促进闭环（全 - 外）-α-生育酚。 该方法可以在不存在或存在添加的溶剂的情况下进行，并且当使用溶剂或溶剂混合物时，溶剂或溶剂混合物的至少一种溶剂组分优选为偶极矩大于9×10-30 Cm（ 或2.7D）。 催化剂的性质是不重要的，但是催化剂优选为硫酸，磷酸，多氟亚烷基磺酸，“NH-酸”，杂多酸，氯化锌，三氟化硼，三氯化铝，或任何f 上述布朗斯台德酸与任何上述路易斯酸。 该过程的产物是维生素E组中工业上最重要的成员中最活跃的产物。

    PROCESS FOR THE MANUFACTURE OF TMHQ
    3.
    发明申请
    PROCESS FOR THE MANUFACTURE OF TMHQ 有权
    TMHQ制造流程

    公开(公告)号：US20130211080A1

    公开(公告)日：2013-08-15

    申请号：US13817012

    申请日：2011-08-25

    申请人： Werner Bonrath ,  Thomas Netscher ,  Jan Schütz ,  Bettina Wüstenberg

    发明人： Werner Bonrath ,  Thomas Netscher ,  Jan Schütz ,  Bettina Wüstenberg

    IPC分类号： C07C45/65 ,  C07D295/116 ,  C07C215/50 ,  C07D311/04 ,  C07D295/096 ,  C07C221/00 ,  C07C45/62

    CPC分类号： C07C45/65 ,  C07C37/002 ,  C07C37/07 ,  C07C45/62 ,  C07C213/00 ,  C07C215/50 ,  C07C221/00 ,  C07D295/096 ,  C07D295/116 ,  C07D311/04 ,  C07C39/08

    摘要： The present invention is directed to a process for the manufacture of 2,3,5-trimethyl-hydro-p-benzoquinone comprising the following steps: a) hydrogenating 2,6-dimethyl-p-benzoquinone with hydrogen in the presence of a hydrogenation catalyst in an organic solvent to obtain 2,6-dimethyl-hydro-p-benzoquinone; b) reacting 2,6-dimethyl-hydro-p-benzoquinone with a secondary amine and formal-dehyde in an organic solvent to obtain 2,6-dimethyl-3-(N,N-disubstituted aminomethyl)-hydro-p-benzoquinone; c) reacting 2,6-dimethyl-3-(N,N-disubstituted aminomethyl)-hydro-p-benzoquinone with hydrogen in the presence of a hydrogenolysis catalyst in an organic solvent to obtain 2,3,5-trimethylhydro-p-benzoquinone; wherein the organic solvent in all steps a), b) and c) is independently selected from the group consisting of methyl tert.-butyl ether, ethyl tert.-butyl ether, tert.-amyl ether, methoxycyclopentane and any mixtures thereof. Preferably the organic solvent used in all steps a), b) and c) is the same.

    摘要翻译： 本发明涉及一种制备2,3,5-三甲基 - 氢 - 对苯醌的方法，包括以下步骤：a）在氢化存在下用氢气氢化2,6-二甲基对苯醌 催化剂在有机溶剂中得到2,6-二甲基 - 氢 - 对苯醌; b）使2,6-二甲基 - 对苯醌与仲胺和正型脱水在有机溶剂中反应，得到2,6-二甲基-3-（N，N-二取代氨基甲基） - 氢对苯醌 ; c）在氢解催化剂存在下，在有机溶剂中使2,6-二甲基-3-（N，N-二取代氨基甲基） - 氢对苯醌与氢气反应，得到2,3,5-三甲基氢对 - 苯醌 其中所有步骤a），b）和c）中的有机溶剂独立地选自甲基叔丁基醚，乙基叔丁基醚，叔戊基醚，甲氧基环戊烷及其任何混合物。 在所有步骤a），b）和c）中使用的有机溶剂优选是相同的。

    ISOMERIZATION OF BETA-KETO-ALLENES
    4.
    发明申请
    ISOMERIZATION OF BETA-KETO-ALLENES 有权
    BETA-KETO-ALLENES的异构体

    公开(公告)号：US20130197272A1

    公开(公告)日：2013-08-01

    申请号：US13642047

    申请日：2011-04-18

    申请人： Werner Bonrath ,  Reinhard Karge ,  Thomas Netscher ,  Yann Pressel

    发明人： Werner Bonrath ,  Reinhard Karge ,  Thomas Netscher ,  Yann Pressel

    IPC分类号： C07C45/67

    CPC分类号： C07C45/67 ,  B01J31/08 ,  B01J2231/52 ,  C07C49/203

    摘要： Isomerization of β-keto-allenes of the general formula I wherein R1 is hydrogen, methyl or ethyl, in particular hydrogen or methyl; R2 is hydrogen or methyl; R3 is hydrogen or methyl, in particular methyl and R4 is an aliphatic hydrocarbon residue containing 1-37 carbon atoms, into corresponding α,γ-dienones of formula II by treatment with a basic ion exchange resin.

    摘要翻译： 其中R 1是氢，甲基或乙基，特别是氢或甲基的通式I的β-酮 - 双烯异构化; R2是氢或甲基; R3是氢或甲基，特别是甲基，R4是含有1-37个碳原子的脂族烃残基，通过用碱性离子交换树脂处理，转化为相应的式II的α，γ-二烯酮。

    Process for the manufacture of chroman derivatives, especially α-tocopherol and alka-noates thereof
    5.
    发明授权
    Process for the manufacture of chroman derivatives, especially α-tocopherol and alka-noates thereof 有权

    公开(公告)号：US08431727B2

    公开(公告)日：2013-04-30

    申请号：US12381127

    申请日：2009-03-06

    申请人： Werner Bonrath ,  Yann Foricher ,  Thomas Netscher ,  Angela Wildermann

    发明人： Werner Bonrath ,  Yann Foricher ,  Thomas Netscher ,  Angela Wildermann

    IPC分类号： C07D311/00 ,  B01J27/06 ,  B01J27/135

    CPC分类号： C07D311/72

    摘要： The present invention relates to novel processes for the manufacture of chroman derivatives such as α-tocopherol (TCP) and alkanoates thereof, especially α-tocopheryl acetate (TCPA), whereby at least one step of the processes is carried out in the presence of a Lewis acid or a mixture of a Lewis acid with a Bronsted acid as the catalyst under pressure, preferably at an absolute pressure of at least 1.1 bar.As starting materials for the manufacture of TCP and its alkanoates either a mixture of 2,3,5-trimethylhydroquinone (TMHQ) or 2,3,6-trimethylhydroquinone-1-alkanoate (TMHQA) and a compound selected from the group consisting of phytol (PH), isophytol (IP) and (iso)phytol derivatives or 2-phytyl-3,5,6-trimethyl-hydroquinone (PTMHQ)/3-phytyl-2,5,6-trimethylhydroquinone-1-alkanoate (PTMHQA) and/or an isomer thereof are used.Suitable Lewis acids are indium(III) salts and scandium(III) salts. Suitable acid mixtures are iron/iron(II) chloride/hydrogen chloride and zinc(II) chloride/hydrogen chloride.

    Isomerization of β-keto-allenes
    8.
    发明授权
    Isomerization of β-keto-allenes 有权
    异构化和共聚物

    公开(公告)号：US08802898B2

    公开(公告)日：2014-08-12

    申请号：US13642047

    申请日：2011-04-18

    申请人： Werner Bonrath ,  Reinhard Karge ,  Thomas Netscher ,  Yann Pressel

    发明人： Werner Bonrath ,  Reinhard Karge ,  Thomas Netscher ,  Yann Pressel

    IPC分类号： C07C45/67

    CPC分类号： C07C45/67 ,  B01J31/08 ,  B01J2231/52 ,  C07C49/203

    摘要： Isomerization of β-keto-allenes of the general formula I wherein R1 is hydrogen, methyl or ethyl, in particular hydrogen or methyl; R2 is hydrogen or methyl; R3 is hydrogen or methyl, in particular methyl and R4 is an aliphatic hydrocarbon residue containing 1-37 carbon atoms, into corresponding α,γ-dienones of formula II by treatment with a basic ion exchange resin.

    摘要翻译： 其中R 1是氢，甲基或乙基，特别是氢或甲基的通式I的双 - 二烯的异构化; R2是氢或甲基; R3是氢或甲基，特别是甲基，R4是含有1-37个碳原子的脂族烃残基，通过碱性离子交换树脂的处理转化为相应的式II的α，γ-二烯酮。

    Process for the manufacture of alkenylated hydroxylated aromatic compounds, of chroman compounds and of their acylated derivatives
    9.
    发明授权
    Process for the manufacture of alkenylated hydroxylated aromatic compounds, of chroman compounds and of their acylated derivatives 有权
    烯基化羟基化芳族化合物，色满化合物及其酰化衍生物的制备方法

    公开(公告)号：US07696364B2

    公开(公告)日：2010-04-13

    申请号：US11005402

    申请日：2004-12-06

    申请人： Werner Bonrath ,  Yann Foricher ,  Thomas Netscher ,  Angela Wildermann

    发明人： Werner Bonrath ,  Yann Foricher ,  Thomas Netscher ,  Angela Wildermann

    IPC分类号： C07D311/11 ,  B01J27/06 ,  B01J27/138

    CPC分类号： C07D311/72 ,  Y02P20/582

    摘要： The present invention relates to a process for the manufacture of alkenylated aromatic compounds featuring at least one hydroxy group, their ring-closure reactions to 5 chroman derivatives, as well as the acylation of the latter and the aromatic compounds featuring at least one hydroxy group themselves. The present invention relates especially to a process for the manufacture of tocol, tocopherols and their alkanoates such as (x-tocopherol (TCP) and alkanoates (TCPA) thereof, preferably (x-toeopheryl acetate (TCPAc). The processes of the present invention are characterized in that at least one step of the processes is carried out in the presence of an indium salt as the catalyst.

    摘要翻译： 本发明涉及一种制备具有至少一个羟基的烯基化芳族化合物的方法，它们与5种苯并二氢吡喃衍生物的闭环反应，以及后者的酰化和具有至少一个羟基的芳族化合物本身 。 本发明特别涉及一种制造多孔，生育酚及其链烷酸酯的方法，例如（x-生育酚（TCP）和链烷酸酯（TCPA）），优选（x-toeopheryl acetate（TCPAc））。本发明的方法 其特征在于，在作为催化剂的铟盐的存在下进行该方法的至少一个步骤。

    Process for the manufacture of chroman derivatives, especially alpha-tocopherol and alka-noates thereof
    10.
    发明申请
    Process for the manufacture of chroman derivatives, especially alpha-tocopherol and alka-noates thereof 有权
    苯并二氢吡喃衍生物，特别是α-生育酚及其烷酸酯的制备方法

    公开(公告)号：US20090176998A1

    公开(公告)日：2009-07-09

    申请号：US12381127

    申请日：2009-03-06

    申请人： Werner Bonrath ,  Yann Foricher ,  Thomas Netscher ,  Angela Wildermann

    发明人： Werner Bonrath ,  Yann Foricher ,  Thomas Netscher ,  Angela Wildermann

    IPC分类号： C07C37/11 ,  C07D311/74

    CPC分类号： C07D311/72

    摘要： The present invention relates to novel processes for the manufacture of chroman derivatives such as α-tocopherol (TCP) and alkanoates thereof, especially α-tocopheryl acetate (TCPA), whereby at least one step of the processes is carried out in the presence of a Lewis acid or a mixture of a Lewis acid with a Bronsted acid as the catalyst under pressure, preferably at an absolute pressure of at least 1.1 bar.As starting materials for the manufacture of TCP and its alkanoates either a mixture of 2,3,5-trimethylhydroquinone (TMHQ) or 2,3,6-trimethylhydroquinone-1-alkanoate (TMHQA) and a compound selected from the group consisting of phytol (PH), isophytol (IP) and (iso)phytol derivatives or 2-phytyl-3,5,6-trimethyl-hydroquinone (PTMHQ)/3-phytyl-2,5,6-trimethylhydroquinone-1-alkanoate (PTMHQA) and/or an isomer thereof are used.Suitable Lewis acids are indium(III) salts and scandium(III) salts. Suitable acid mixtures are iron/iron(II) chloride/hydrogen chloride and zinc(II) chloride/hydrogen chloride.

    摘要翻译： 本发明涉及制造色氨酸衍生物如α-生育酚（TCP）及其链烷酸酯，特别是α-生育酚乙酸酯（TCPA）的新方法，其中至少一个步骤的方法是在 路易斯酸或路易斯酸与布朗斯台德酸的混合物作为催化剂，优选在至少1.1巴的绝对压力下进行。 作为制备TCP及其链烷酸酯的起始原料是2,3,5-三甲基氢醌（TMHQ）或2,3,6-三甲基氢醌-1-链烷酸酯（TMHQA）的混合物和选自植醇 （PH），异植醇（IP）和（异）植醇衍生物或2-植酰基-3,5,6-三甲基 - 氢醌（PTMHQ）/ 3-植酰基-2,5,6-三甲基氢醌-1-链烷酸酯（PTMHQA） 和/或其异构体。 合适的路易斯酸是铟（III）盐和钪（III）盐。 合适的酸混合物是氯化铁/氯化铁（II）/氯化氢和氯化锌（II）/氯化氢。