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    Manufacture of α-tocopherol
    2.
    发明授权
    Manufacture of α-tocopherol 有权
    α-生育酚的制造

    公开(公告)号：US07153984B2

    公开(公告)日：2006-12-26

    申请号：US10535603

    申请日：2003-09-30

    申请人： Werner Bonrath ,  Alois Haas ,  Simone Hoppmann ,  Thomas Netscher ,  Horst Pauling

    发明人： Werner Bonrath ,  Alois Haas ,  Simone Hoppmann ,  Thomas Netscher ,  Horst Pauling

    IPC分类号： C07D311/72

    CPC分类号： C07D311/72

    摘要： A process for the manufacture of (all-rac)-α-tocopherol by the acid-catalyzed reaction of trimethylhydroquinone with isophytol or phytol is characterized by carrying out the reaction in the presence of methane trisulphonate as the catalyst in an organic solvent. The product of the process is the most active and industrially most important member of the vitamin E group.

    摘要翻译： 通过三甲基氢醌与异麦芽糖醇或植醇酯的酸催化反应制备（全外消旋）-α-生育酚的方法的特征在于在甲磺酸三磺酸盐作为催化剂存在下在有机溶剂中进行反应。 该过程的产物是维生素E组中最活跃和最具工业最重要的成员。

    Tocopherol manufacture by tris(perfluorohydrocarbylsulphonyl) methane or metal methides thereof
    3.
    发明授权
    Tocopherol manufacture by tris(perfluorohydrocarbylsulphonyl) methane or metal methides thereof 有权
    由三（全氟代烃基磺酰基）甲烷或其金属甲基化物制造的生育酚

    公开(公告)号：US06369242B2

    公开(公告)日：2002-04-09

    申请号：US09802272

    申请日：2001-03-08

    申请人： Werner Bonrath ,  Alois Haas ,  Eike Hoppmann ,  Thomas Netscher ,  Horst Pauling

    发明人： Werner Bonrath ,  Alois Haas ,  Eike Hoppmann ,  Thomas Netscher ,  Horst Pauling

    IPC分类号： C07D31104

    CPC分类号： C07D311/72

    摘要： A method of making (all-rac.)-&agr;-tocopherol by the acid-catalyzed condensation of trimethylhydroquinone with isophytol or phytol wherein the condensation is carried out in the presence of a tris(perfluoroalkanesulphonyl or pentafluorobenzenesulphonyl)methane or a metal salt thereof as the catalyst in an organic solvent. In addition to the metal salt, a Bronsted acid, e.g. sulfuric acid, phosphoric acid or p-toluenesulphonic acid, may be used as a co-catalyst. The product of the method of making is the most active member of the vitamin E group.

    摘要翻译： 通过三甲基氢醌与异植醇或植醇的酸催化缩合制备（全外消旋）-α-生育酚的方法，其中缩合在三（全氟烷基磺酰基或五氟苯磺酰基）甲烷或其金属盐存在下进行，为 该催化剂在有机溶剂中。 除了金属盐，布朗斯台德酸，例如， 硫酸，磷酸或对甲苯磺酸可用作助催化剂。 制作方法的产物是维生素E组中最活跃的成员。

    Method of making (all-rac)-&agr;-tocopherol
    4.
    发明授权
    Method of making (all-rac)-&agr;-tocopherol 有权
    制造（全脱色）-α-生育酚的方法

    公开(公告)号：US06482961B2

    公开(公告)日：2002-11-19

    申请号：US09931663

    申请日：2001-08-16

    申请人： Werner Bonrath ,  Alois Haas ,  Eike Hoppmann ,  Horst Pauling

    发明人： Werner Bonrath ,  Alois Haas ,  Eike Hoppmann ,  Horst Pauling

    IPC分类号： C07D31104

    CPC分类号： C07D311/72

    摘要： The present invention is a method of making (all-rac)-&agr;-tocopherol in a reaction having the following steps: a) reacting trimethylhydroquinone and a phytol selected from the group consisting of isophytol and phytol in the presence of a bis(perfluorinated hydrocarbyl sulphonyl)imide catalyst or a metal salt thereof of formula I: [(R1SO2)2N]xR2  (I)  wherein each R1, independently, signifies a perfluoroalkyl group CnF2n+1 or a pentafluorophenyl, or both symbols R1 together signify a poly-difluoromethylene group—(CF2)m—, with the proviso that both symbols R1 cannot simultaneously signify trifluoromethyl, R2 signifies a proton or a cationic form of a metal selected from the group consisting of boron, magnesium, aluminum, silicon, scandium, titanium, vanadium, manganese, iron, cobalt, nickel, copper, zinc, yttrium, zirconium, rhodium, palladium, silver, tin, lanthanum, cerium, praseodymium, neodymium, europium, dysprosium, thulium, ytterbium, hafnium, platinum, and gold, m is an integer from 2 to 4, n is an integer from 1 to 10, and x is the corresponding valency of the proton (1) or the metal cation (1, 2, 3, or 4), in organic solvent; and b) recovering (all-rac)-&agr;-tocopherol from the reaction mixture.

    摘要翻译： 本发明是在具有以下步骤的反应中制备（全脱氧）-α-生育酚的方法：a）在双（全氟化烃基）的存在下，使三甲基对苯二酚和选自异麦芽糖醇和植醇的植醇 磺酰基）酰亚胺催化剂或其金属盐：其中R1独立地表示全氟烷基CnF2n + 1或五氟苯基，或两个符号R1一起表示聚二氟亚甲基 - （CF 2）m - ，条件是 两个符号R1不能同时表示三氟甲基，R2表示选自硼，镁，铝，硅，钪，钛，钒，锰，铁，钴，镍，铜等的金属的质子或阳离子形式。 锌，钇，锆，铑，钯，银，锡，镧，铈，镨，钕，铕，镝，ium，镱，铪，铂和金，m为2〜4的整数，n为 ger为1至10，andx为有机溶剂中质子（1）或金属阳离子（1,2,3或4）的相应化合价; 和b）从反应混合物中回收（全 - 外）-α-生育酚。

    Process for the manufacture of 5-cyano-4-lower alkyl-oxazoles
    6.
    发明授权
    Process for the manufacture of 5-cyano-4-lower alkyl-oxazoles 失效
    制备5-氰基-4-低级烷基 - 恶唑的方法

    公开(公告)号：US5910594A

    公开(公告)日：1999-06-08

    申请号：US8793

    申请日：1998-01-20

    申请人： Klaus Behringer ,  Werner Bonrath ,  Horst Pauling

    发明人： Klaus Behringer ,  Werner Bonrath ,  Horst Pauling

    IPC分类号： B01J31/02 ,  C07B61/00 ,  C07D263/34 ,  C07D263/30 ,  C07D263/36 ,  C07D263/44

    CPC分类号： C07D263/34

    摘要： A process for the manufacture of a 5-cyano-4-lower alkyl-oxazole by the dehydration of a 5-carbamoyl-4-lower alkyl-oxazole is disclosed. The reaction is carried out by dehydrating the oxazole with silicon tetrachloride in the presence of an amine in an aprotic organic solvent. 5-Carbamoyl-4-methyl-oxazole may be dehydrated by the process in accordance with the invention to obtain 5-cyano-4-methyl-oxazole, which is a valuable intermediate in the synthesis of pyridoxine.

    摘要翻译： 公开了通过5-氨基甲酰基-4-低级烷基 - 恶唑脱水制备5-氰基-4-低级烷基恶唑的方法。 该反应通过在胺存在下在四氢呋喃中在非质子有机溶剂中脱水来进行。 5-氨基甲酰基-4-甲基恶唑可以通过本发明的方法脱水得到5-氰基-4-甲基恶唑，它是合成吡哆醇的有价值的中间体。

    Method of making D,L-A-tocopherol
    7.
    发明授权
    Method of making D,L-A-tocopherol 失效
    制备D，L-A-生育酚的方法

    公开(公告)号：US5908939A

    公开(公告)日：1999-06-01

    申请号：US951273

    申请日：1997-10-16

    申请人： Marcel Baak ,  Werner Bonrath ,  Horst Pauling

    发明人： Marcel Baak ,  Werner Bonrath ,  Horst Pauling

    IPC分类号： B01J31/02 ,  C07B61/00 ,  C07D311/00 ,  C07D311/72 ,  C07D311/02

    CPC分类号： C07D311/72

    摘要： A process for the manufacture of d,1-.alpha.-tocopherol by the catalyzed condensation of trimethylhydroquinone with isophytol comprises carrying out the condensation in the presence of bis-(trifluoromethylsulphonyl)amine �HN(SO.sub.2 CF.sub.3).sub.2 ! or a metal salt thereof of the formula Met �N(SO.sub.2 CF.sub.3).sub.2 !.sub.n (I), wherein Met signifies a metal atom selected from the group of lithium, boron, magnesium, aluminium, silicon, scandium, titanium, vanadium, manganese, iron, cobalt, nickel, copper, zinc, yttrium, zirconium, rhodium, palladium, silver, tin, lanthanum, cerium, neodymium, praseodymium, europium, dysprosium, ytterbium, hafnium, platinum and gold and n signifies the corresponding valency (1, 2, 3, or 4) of the metal atom Met, as the catalyst or of a combination of a metal salt of formula I and a strong Bronsted acid as the catalyst system in an organic solvent. The product of the process is the most active member of the vitamin E group.

    摘要翻译： 通过三甲基氢醌与异植醇的催化缩合制备d，1-α-生育酚的方法包括在双（三氟甲基磺酰基）胺[HN（SO 2 CF 3）2]或其金属盐存在下进行缩合 其中Met表示选自锂，硼，镁，铝，硅，钪，钛，钒，锰，铁，钴，镍，铜中的金属原子的Met [N（SO 2 CF 3）2] n（I） ，锌，钇，锆，铑，钯，银，锡，镧，铈，钕，镨，铕，镝，镱，铪，铂和金，n表示相应的化合价（1,2,3或4） 的金属原子Met作为催化剂或式I的金属盐与强布朗斯台德酸的组合作为有机溶剂中的催化剂体系。 该过程的产物是维生素E组中最活跃的成员。

    Method for the dehydration of amides to nitriles
    8.
    发明授权
    Method for the dehydration of amides to nitriles 失效
    将酰胺脱水为腈的方法

    公开(公告)号：US5817827A

    公开(公告)日：1998-10-06

    申请号：US734987

    申请日：1996-10-22

    申请人： Werner Bonrath ,  Horst Pauling

    发明人： Werner Bonrath ,  Horst Pauling

    IPC分类号： C07C253/20 ,  C07C255/03 ,  C07C255/50 ,  C07C255/52 ,  C07D213/84 ,  C07D213/85 ,  C07D263/34 ,  C07C253/00 ,  C07D211/78

    CPC分类号： C07D213/84 ,  C07C253/20 ,  C07D213/85 ,  C07D263/34

    摘要： The present invention relates to a process for the dehydration of amides to nitrites which comprises carrying out the dehydration in the presence of an adduct of sulphur trioxide and an amine as the dehydrating reagent in a basic reaction mixture. Thereby, for example, aliphatic, aromatic and heteroaromatic amides are dehydrated to the corresponding nitrites, such as 5-carbamoyl-4-methyl-oxazole to 5-cyano-4-methyl-oxazole, a valuable intermediate in the synthesis of pyridoxine.

    摘要翻译： 本发明涉及一种将酰胺脱水成亚硝酸盐的方法，包括在碱性反应混合物中，在三氧化硫和胺作为脱水剂的加合物存在下进行脱水。 因此，例如，将脂族，芳族和杂芳族酰胺脱水成相应的亚硝酸盐，例如5-氨基甲酰基-4-甲基 - 恶唑，得到5-氰基-4-甲基恶唑，其是合成吡哆醇的有价值的中间体。

    PROCESS FOR THE MANUFACTURE OF TMHQ
    10.
    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。