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1. 发明授权

US08431727B2 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.

2. 发明申请

US20050171362A1 Process for the manufacture of alkenylated hydroxylated aromatic compounds, of chroman compounds and of their acylated derivatives 有权
标题翻译：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：US20050171362A1
公开(公告)日：2005-08-04
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： C07C37/11 , C07D311/58 , C07D311/72 , C07D311/74
CPC分类号： C07D311/72 , Y02P20/582
摘要： The present invention relates to a novel process for the manufacture of alkenylated aromatic compounds featuring at least one hydroxy group, their ring-closure reactions to 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 α-tocopherol (TCP) and alkanoates (TCPA) thereof, preferably α-tocopheryl 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. Thus, an object of the present invention is the use of an indium salt as the catalyst in Friedel-Crafts alkylation reactions of aromatic compounds featuring at least one hydroxy group and ring-closure reactions of the latter to produce chroman-ring compounds in organic solvents. According to another aspect of the invention indium salts can be used as the catalyst in processes for the manufacture of tocyl alkanoates, tocopheryl alkanoates and alkanoates of aromatic compounds featuring at least one hydroxy group by reacting tocols, tocopherol and aromatic compounds featuring at least one hydroxy group, respectively, with an acylating agent. Suitable indium salts are indium(III) salts, especially indium trichloride, indium tribromide or indium triiodide, indium(III) triflate, indium(III) bis(trifluoromethanesulfonamide) and indium(III) acetate. In preferred embodiments of the invention the processes are carried out at a pressure of at least 0.96 bar, whereby the acylation can be carried out at an absolute pressure of at least 0.02 bar.
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新方法，它们对苯并二氢吡喃衍生物的闭环反应以及后者的酰化反应和具有至少一个羟基的芳族化合物本身。本发明尤其涉及一种生产托生物，生育酚及其链烷酸酯如α-生育酚（TCP）和链烷酸酯（TCPA），优选醋酸α-生育酚酯（TCPAc）的方法。本发明的方法的特征在于，在作为催化剂的铟盐存在下进行至少一个步骤。因此，本发明的目的是在Friedel-Crafts烷基化反应中使用铟盐作为催化剂，其特征在于具有至少一个羟基和后者的闭环反应，在有机溶剂中产生苯并二氢吡喃酮化合物。根据本发明的另一方面，铟盐可以用作制备烷基链烷酸酯，生育酚基链烷酸酯和具有至少一个羟基的芳族化合物的链烷酸酯的方法，所述芳族化合物是通过使醇，生育酚和具有至少一个羟基的芳香族化合物分别与酰化剂。合适的铟盐是铟（III）盐，特别是三氯化铟，三溴化铟或三碘化铟，三氟甲磺酸铟（III），三（三氟甲烷磺酰胺）铟（III）和乙酸铟（III））。在本发明的优选实施方案中，该方法在至少0.96巴的压力下进行，由此酰化可以在至少0.02巴的绝对压力下进行。

3. 发明申请

US20050277777A1 Process for the manufacture of chroman derivatives, especially alpha-tocopherol and alkanoates thereof 审中-公开
标题翻译：苯并二氢吡喃衍生物，特别是α-生育酚及其链烷酸酯的制备方法
公开(公告)号：US20050277777A1
公开(公告)日：2005-12-15
申请号：US11005113
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： C07D311/00 , C07D311/72 , 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。

4. 发明授权

US07696364B2 Process for the manufacture of alkenylated hydroxylated aromatic compounds, of chroman compounds and of their acylated derivatives 有权
标题翻译：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。

5. 发明申请

US20090176998A1 Process for the manufacture of chroman derivatives, especially alpha-tocopherol and alka-noates thereof 有权
标题翻译：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。

6. 发明申请

US20110144358A1 Process for the manufacture of trimethylhydroquinone dialkanoates 审中-公开
标题翻译：制造三甲基对苯二酚二链烷酸酯的方法
公开(公告)号：US20110144358A1
公开(公告)日：2011-06-16
申请号：US12929835
申请日：2011-02-18
申请人： Werner Bonrath , Yann Foricher
发明人： Werner Bonrath , Yann Foricher
IPC分类号： C07D311/04 , C07D311/00 , C07C39/10
CPC分类号： C07C67/00 , C07C69/017 , C07C69/16
摘要： The present invention is directed to a process for the manufacture of a 2,3,5-trimethylhydroquinone dialkanoate comprising reacting ketoisophorone with an acylating agent in the presence of an indium salt as the catalyst. Preferred are indium(III) salts such as indium trichloride or indium tris (trifluoromethanesulfonate). Further aspects of the present invention are a process for the manufacture of 2,3,5-trimethylhydroquinone using 2,3,5-trimethylhydroquinone dialkanoate as the starting material, especially a process for the manufacture of 2,3,5-trimethylhydroquinone by transesterification of 2,3,5-trimethylhydroquinone dialkanoate, as well as a process for the manufacture of a-tocopherol and its alkanoates, especially of (all-rac)-a-tocopherol and its acetate, comprising the reaction of ketoisophorone to 2,3,5-trimethylhydroquinone dialkanoate according to the present invention. Furthermore, the present invention also deals with a process for the manufacture of formulations of a-tocopherol and its alkanoates, especially of formulations of (all-rac)-a-tocopherol and its acetate, comprising the reaction of ketoisophorone to 2,3,5-trimethylhydroquinone dialkanoate according to the present invention.
摘要翻译：本发明涉及一种制备2,3,5-三甲基氢醌二链烷酸酯的方法，其包括在铟盐作为催化剂存在下使酮异佛尔酮与酰化剂反应。优选铟（III）盐如三氯化铟或三（三氟甲磺酸）铟。本发明的其它方面是使用2,3,5-三甲基氢醌二链烷酸酯作为原料制造2,3,5-三甲基氢醌的方法，特别是通过酯交换制备2,3,5-三甲基氢醌的方法 2,3,5-三甲基氢醌二链烷酸酯，以及一种生产α-生育酚及其链烷酸酯，特别是（全脱氧）-α-生育酚及其乙酸酯的方法，包括酮异二酮与2,3 ，根据本发明的5-三甲基氢醌二链烷酸酯。此外，本发明还涉及生产α-生育酚及其链烷酸酯，特别是（全脱氧）-α-生育酚及其乙酸酯的制剂的制剂的方法，其包括酮异二酮与2,3,4- 按照本发明的5-三甲基氢醌二链烷酸酯。

7. 发明申请

US20070049762A1 Process for the manufacture of trimethylydroquine dialkanoates 审中-公开
标题翻译：制造三甲基二氨基二烷酸酯的方法
公开(公告)号：US20070049762A1
公开(公告)日：2007-03-01
申请号：US10582672
申请日：2004-12-07
申请人： Werner Bonrath , Yann Foricher
发明人： Werner Bonrath , Yann Foricher
IPC分类号： C07D311/00
CPC分类号： C07C67/00 , C07C69/017 , C07C69/16
摘要： The present invention is directed to a process for the manufacture of a 2,3,5-trimethyl-hydroquinone dialkanoate comprising reacting ketoisophorone with an acylating agent in the presence of an indium salt as the catalyst. Preferred are indium(III) salts such as indium trichloride or indium tris(trifluoromethanesulfonate). Further aspects of the present invention are a process for the manufacture of 2,3,5-tri-methylhydroquinone using 2,3,5-trimethylhydroquinone dialkanoate as the starting mate-rial, especially a process for the manufacture of 2,3,5-trimethylhydroquinone by trans-esterification of 2,3,5-trimethylhydroquinone dialkanoate, as well as a process for the manufacture of a-tocopherol and its alkanoates, especially of (all-rac)-a-tocopherol and its acetate, comprising the reaction of ketoisophorone to 2,3,5-trimethylhydroquinone dialka-noate according to the present invention. Furthermore, the present invention also deals with a process for the manufacture of formulations of a-tocopherol and its alkanoates, especially of formulations of (all-rac)-a-tocopherol and its acetate, comprising the reaction of ketoisophorone to 2,3,5-trimethylhydroquinone dialkanoate according to the present invention.
摘要翻译：本发明涉及一种制备2,3,5-三甲基 - 氢醌二链烷酸酯的方法，其包括在铟盐作为催化剂存在下使酮异佛尔酮与酰化剂反应。优选铟（III）盐如三氯化铟或三（三氟甲磺酸）铟。本发明的另外的方面是使用2,3,5-三甲基氢醌二链烷酸酯作为起始材料制造2,3,5-三甲基氢醌的方法，特别是制备2,3,5三通过2,3,5-三甲基氢醌二链烷酸酯的酯交换，以及一种制备α-生育酚及其链烷酸酯，特别是（全脱氨基）-α-生育酚及其乙酸酯的方法，该方法包括反应的酮异佛尔酮至根据本发明的2,3,5-三甲基对苯二酚二乙酸酯。此外，本发明还涉及生产α-生育酚及其链烷酸酯，特别是（全脱氧）-α-生育酚及其乙酸酯的制剂的制剂的方法，其包括酮异二酮与2,3,4- 按照本发明的5-三甲基氢醌二链烷酸酯。

8. 发明申请

US20090221860A1 TRANSPORT OF ETHYNE IN FORM OF A-ALKYNOLS AS ETHYNE PRECURSORS 有权
标题翻译：乙腈在乙腈前驱体中的运输
公开(公告)号：US20090221860A1
公开(公告)日：2009-09-03
申请号：US12298371
申请日：2007-03-30
申请人： Angela Wildermann , Werner Bonrath , Gunther Hellmann
发明人： Angela Wildermann , Werner Bonrath , Gunther Hellmann
IPC分类号： C07C7/20
CPC分类号： C07C29/42 , C07C1/20 , C07C7/20 , C07C11/24 , C10L3/02 , C07C33/042 , C07C33/048
摘要： The present invention relates to a new method for a safe transport of ethyne in form of α-alkynols as precursors for ethyne. The new method comprises three steps. In a first step the synthesis of the α-alkynol(s) is performed by reacting ethyne with (a) carbonyl compound(s). The second step comprises the transport of the resulting α-alkynol(s) in a safe manner, whereas the safety requirements for this transport are not as high as for ethyne because α-alkynol(s) are normally classified for transportation as hazardous class 3. In the third step the α-alkynol(s) can be cleaved and the ethyne and the carbonyl compound(s) can be obtained in the cleavage reaction and can be separated to yield pure products for further applications.
摘要翻译：本发明涉及一种以α-炔醇形式的乙炔安全运输作为乙炔前体的新方法。新方法包括三个步骤。在第一步中，α-炔醇的合成通过使乙炔与（a）羰基化合物反应来进行。第二步包括以安全的方式运输所得的α-炔醇，而这种运输的安全要求不如乙炔那么高，因为α-炔醇通常被分类为危险品类3 在第三步中，可以裂解α-炔醇，并且可以在裂解反应中获得乙炔和羰基化合物，并且可以分离以产生用于进一步应用的纯产物。

9. 发明授权

US08003843B2 Transport of ethyne in form of α-alkynols as ethyne precursors 有权
标题翻译：以α-炔醇形式的乙炔转运乙炔前体
公开(公告)号：US08003843B2
公开(公告)日：2011-08-23
申请号：US12298371
申请日：2007-03-30
申请人： Angela Wildermann , Werner Bonrath , Gunther Hellmann
发明人： Angela Wildermann , Werner Bonrath , Gunther Hellmann
IPC分类号： C07C7/20
CPC分类号： C07C29/42 , C07C1/20 , C07C7/20 , C07C11/24 , C10L3/02 , C07C33/042 , C07C33/048
摘要： The present invention relates to a new method for a safe transport of ethyne in form of α-alkynols as precursors for ethyne. The new method comprises three steps. In a first step the synthesis of the α-alkynol(s) is performed by reacting ethyne with (a) carbonyl compound(s). The second step comprises the transport of the resulting α-alkynol(s) in a safe manner, whereas the safety requirements for this transport are not as high as for ethyne because α-alkynol(s) are normally classified for transportation as hazardous class 3. In the third step the α-alkynol(s) can be cleaved and the ethyne and the carbonyl compound(s) can be obtained in the cleavage reaction and can be separated to yield pure products for further applications.
摘要翻译：本发明涉及以乙炔为前体的α-炔醇形式的乙炔的安全运输的新方法。新方法包括三个步骤。在第一步中，α-炔醇的合成通过使乙炔与（a）羰基化合物反应来进行。第二步包括以安全的方式运输所得的α-炔醇，而这种运输的安全要求不如乙炔那么高，因为α-炔醇通常被分类为运输危险品3 在第三步中，可以裂解α-炔醇，并且可以在裂解反应中获得乙炔和羰基化合物，并且可以分离得到用于进一步应用的纯产物。

10. 发明授权

US09067877B2 Process for the production of 1,3,3-trimethyl-2-(3-methylpent-2-en-4-ynyl)cyclohex-1-ene 有权
标题翻译：制备1,3,3-三甲基-2-（3-甲基戊-2-烯-4-炔基）环己-1-烯的方法
公开(公告)号：US09067877B2
公开(公告)日：2015-06-30
申请号：US14128741
申请日：2012-06-14
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： C07C1/24 , C07C403/02 , C07C403/16 , C07C403/08 , C07C403/24
CPC分类号： C07C403/24 , C07C1/24 , C07C2/86 , C07C13/20 , C07C403/02 , C07C403/08 , C07C403/16 , C07C2601/16
摘要： The present invention relates to an improved process for the production of 1,3,3-trimethyl-2-(3-methylpent-2-en-4-ynyl)cyclohex-1-ene, highly enriched in the Z-isomer, and the use of such compounds in organic syntheses, especially in processes forming intermediates (building blocks) the synthesis of vitamin A or β-carotene or other carotenoids, e.g. canthaxanthin, astaxanthin or zeaxanthin.
摘要翻译：本发明涉及生产高度富含Z-异构体的1,3,3-三甲基-2-（3-甲基戊-2-烯-4-炔基）环己-1-烯的改进方法，以及这些化合物在有机合成中的应用，特别是在形成中间体（构建块）的过程中合成维生素A或其组合物 - 胡萝卜素或其他类胡萝卜素，例如角黄素，虾青素或玉米黄质。

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