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1. 发明授权

US08318985B2 Method for producing optically active, racemic menthol 有权
标题翻译：光学活性外消旋薄荷醇的制备方法
公开(公告)号：US08318985B2
公开(公告)日：2012-11-27
申请号：US12744110
申请日：2008-11-13
申请人： Gunnar Heydrich , Gabriele Gralla , Matthias Rauls , Joachim Schmidt-Leithoff , Klaus Ebel , Wolfgang Krause , Steffen Oehlenschläger , Christoph Jäkal , Marko Friedrich , Eike Johannes Bergner , Nawid Kashani-Shirazi , Rocco Paciello
发明人： Gunnar Heydrich , Gabriele Gralla , Matthias Rauls , Joachim Schmidt-Leithoff , Klaus Ebel , Wolfgang Krause , Steffen Oehlenschläger , Christoph Jäkal , Marko Friedrich , Eike Johannes Bergner , Nawid Kashani-Shirazi , Rocco Paciello
IPC分类号： C07C29/17
CPC分类号： C07C29/56 , C07B2200/07 , C07C29/172 , C07C29/78 , C07C45/62 , C07C45/82 , C07C2601/14 , C07C2601/16 , C07C47/21 , C07C35/12 , C07C35/17
摘要： The present invention relates to a particularly economic overall method for producing menthol, specifically for producing optically active, essentially enantiomerically and diastereomerically pure L-menthol and racemic menthol, starting from the starting material citral which is available inexpensively on an industrial scale. The method comprises the following stepsa) catalytic hydrogenation of neral and/or geranial to give citronellal,b) cyclization of citronellal to isopulegol in the presence of an acidic catalyst,c) purification of isopulegol by crystallization andd) catalytic hydrogenation of isopulegol to give menthol.
摘要翻译：本发明涉及一种特别经济的制备薄荷醇的总体方法，特别用于制备光学活性的，基本上是对映异构体和非对映异构体纯的L-薄荷醇和外消旋薄荷醇，其原料柠檬醛以工业规模廉价地得到。该方法包括以下步骤：a）在酸性催化剂存在下，通过催化氢化醛和/或香叶醇以产生香茅醛，b）在酸性催化剂的存在下将香茅醛环化成异葎草醇，c）通过结晶纯化异丙醇钾，和d）将异丙醇的催化氢化至给薄荷脑

2. 发明申请

US20100249467A1 METHOD FOR PRODUCING OPTICALLY ACTIVE, RACEMIC MENTHOL 有权
标题翻译：用于生产光学活性的，法定的MENTHOL的方法
公开(公告)号：US20100249467A1
公开(公告)日：2010-09-30
申请号：US12744110
申请日：2008-11-13
申请人： Gunnar Heydrich , Gabriele Gralla , Matthias Rauls , Joachim Schmidt-Leithoff , Klaus Ebel , Wolfgang Krause , Steffen Oehlenschläger , Christoph Jäkel , Marko Friedrich , Eike Johannes Bergner , Nawid Kashani-Shirazi , Rocco Paciello
发明人： Gunnar Heydrich , Gabriele Gralla , Matthias Rauls , Joachim Schmidt-Leithoff , Klaus Ebel , Wolfgang Krause , Steffen Oehlenschläger , Christoph Jäkel , Marko Friedrich , Eike Johannes Bergner , Nawid Kashani-Shirazi , Rocco Paciello
IPC分类号： C07C35/12
CPC分类号： C07C29/56 , C07B2200/07 , C07C29/172 , C07C29/78 , C07C45/62 , C07C45/82 , C07C2601/14 , C07C2601/16 , C07C47/21 , C07C35/12 , C07C35/17
摘要： The present invention relates to a particularly economic overall method for producing menthol, specifically for producing optically active, essentially enantiomerically and diastereomerically pure L-menthol and racemic menthol, starting from the starting material citral which is available inexpensively on an industrial scale. The method comprises the following stepsa.1) catalytic hydrogenation of neral and/or geranial to give citronellal, b.1) cyclization of citronellal to isopulegol in the presence of an acidic catalyst, c.1) purification of isopulegol by crystallization and d.1) catalytic hydrogenation of isopulegol to give menthol.
摘要翻译：本发明涉及一种特别经济的制备薄荷醇的总体方法，特别用于制备光学活性的，基本上是对映异构体和非对映异构体纯的L-薄荷醇和外消旋薄荷醇，其原料柠檬醛以工业规模廉价地得到。该方法包括以下步骤a.1）在酸性催化剂的存在下，将柠檬醛和/或香叶醇进行催化氢化以产生香茅醛，b.1）将香茅醛环化成异胡仑醇，c.1）通过结晶和d进行异丙醇的纯化 .1）异丙醇的催化氢化得到薄荷醇。

3. 发明授权

US08414744B2 Continuous process for preparing menthol in pure or enriched form 有权
标题翻译：用于制备纯粹或富集形式的薄荷醇的连续方法
公开(公告)号：US08414744B2
公开(公告)日：2013-04-09
申请号：US12677688
申请日：2008-07-23
申请人： Gunnar Heydrich , Gabriele Gralla , Klaus Ebel , Wolfgang Krause , Nawid Kashani-Shirazi
发明人： Gunnar Heydrich , Gabriele Gralla , Klaus Ebel , Wolfgang Krause , Nawid Kashani-Shirazi
IPC分类号： B01D3/14
CPC分类号： B01D3/141 , B01D3/14 , C07B2200/07 , C07C29/80 , C07C2601/14 , C07C35/12 , C07C35/17
摘要： The present invention relates to a continuous process for preparing racemic or optically active menthol in pure or enriched form by distillatively separating menthol from substance mixtures which comprise essentially menthol and diastereomers thereof. This distillatiive separation is performed in a dividing wall column with 50 to 300 theoretical plates and one or more side draw points at an absolute operating pressure of 5 to 500 mbar.
摘要翻译：本发明涉及通过将薄荷醇与基本上含有薄荷醇和非对映异构体的物质混合物蒸馏分离来制备纯的或富集形式的外消旋或光学活性薄荷醇的连续方法。该蒸馏分离在具有50至300个理论塔板和一个或多个侧向牵引点的分隔壁塔中进行，绝对操作压力为5至500毫巴。

4. 发明申请

US20130046118A1 METHOD FOR PRODUCING OPTICALLY ACTIVE, RACEMIC MENTHOL 审中-公开
标题翻译：用于生产光学活性的，法定的MENTHOL的方法
公开(公告)号：US20130046118A1
公开(公告)日：2013-02-21
申请号：US13658003
申请日：2012-10-23
申请人： Gunnar Heydrich , Gabriele Gralla , Matthias Rauls , Joachim Schmidt-Leithoff , Klaus Ebel , Wolfgang Krause , Steffen Oehlenschläger , Christoph Jäkel , Marko Friedrich , Eike Johannes Bergner , Nawid Kashani-Shirazi , Rocco Paciello
发明人： Gunnar Heydrich , Gabriele Gralla , Matthias Rauls , Joachim Schmidt-Leithoff , Klaus Ebel , Wolfgang Krause , Steffen Oehlenschläger , Christoph Jäkel , Marko Friedrich , Eike Johannes Bergner , Nawid Kashani-Shirazi , Rocco Paciello
IPC分类号： C07C29/17
CPC分类号： C07C29/56 , C07B2200/07 , C07C29/172 , C07C29/78 , C07C45/62 , C07C45/82 , C07C2601/14 , C07C2601/16 , C07C47/21 , C07C35/12 , C07C35/17
摘要： The present invention relates to a particularly economic overall method for producing menthol, specifically for producing optically active, essentially enantiomerically and diastereomerically pure L-menthol and racemic menthol, starting from the starting material citral which is available inexpensively on an industrial scale. The method comprises the following steps a.1) catalytic hydrogenation of neral and/or geranial to give citronellal, b.1) cyclization of citronellal to isopulegol in the presence of an acidic catalyst, c.1) purification of isopulegol by crystallization and d.1) catalytic hydrogenation of isopulegol to give menthol.
摘要翻译：本发明涉及一种特别经济的制备薄荷醇的总体方法，特别用于制备光学活性的，基本上是对映异构体和非对映异构体纯的L-薄荷醇和外消旋薄荷醇，其原料柠檬醛以工业规模廉价地得到。该方法包括以下步骤a.1）在酸性催化剂的存在下，将柠檬醛和/或香叶醇进行催化氢化以产生香茅醛，b.1）将香茅醛环化成异胡仑醇，c.1）通过结晶和d进行异丙醇的纯化 .1）异丙醇的催化氢化得到薄荷醇。

5. 发明申请

US20100206712A1 CONTINUOUS PROCESS FOR PREPARING MENTHOL IN PURE OR ENRICHED FORM 有权
标题翻译：用于制备纯净或增强形式的MENTHOL的连续方法
公开(公告)号：US20100206712A1
公开(公告)日：2010-08-19
申请号：US12677688
申请日：2008-07-23
申请人： Gunnar Heydrich , Gabriele Gralla , Klaus Ebel , Wolfgang Krause , Nawid Kashani-Shirazi
发明人： Gunnar Heydrich , Gabriele Gralla , Klaus Ebel , Wolfgang Krause , Nawid Kashani-Shirazi
IPC分类号： C07C29/80 , B01D3/14 , B01J19/00 , C07C35/12
CPC分类号： B01D3/141 , B01D3/14 , C07B2200/07 , C07C29/80 , C07C2601/14 , C07C35/12 , C07C35/17
摘要： The present invention relates to a continuous process for preparing racemic or optically active menthol in pure or enriched form by distillatively separating menthol from substance mixtures which comprise essentially menthol and diastereomers thereof. This distillatiive separation is performed in a dividing wall column with 50 to 300 theoretical plates and one or more side draw points at an absolute operating pressure of 5 to 500 mbar.
摘要翻译：本发明涉及通过将薄荷醇与基本上含有薄荷醇和非对映异构体的物质混合物蒸馏分离来制备纯的或富集形式的外消旋或光学活性薄荷醇的连续方法。该蒸馏分离在具有50至300个理论塔板和一个或多个侧向牵引点的分隔壁塔中进行，绝对操作压力为5至500毫巴。

6. 发明申请

US20100312020A1 METHOD FOR THE PRODUCTION OF 4,4'-[1-TRIFLUOROMETHYL)ALKYLIDENE]-BIS-(2,6-DIPHENYLPHENOLS) 有权
标题翻译：生产4,4' - [1-三氟甲基）亚苄基] -BIS-（2,6-二苯基苯酚）的方法
公开(公告)号：US20100312020A1
公开(公告)日：2010-12-09
申请号：US12808865
申请日：2008-12-17
申请人： Gabriele Gralla , Gunnar Heydrich , Klaus Ebel , Wolfgang Krause
发明人： Gabriele Gralla , Gunnar Heydrich , Klaus Ebel , Wolfgang Krause
IPC分类号： C07C37/62 , C07C37/00
CPC分类号： C07C45/74 , C07C37/07 , C07C37/20 , C07C37/62 , C07C49/613 , C07C49/653 , C07C39/15 , C07C39/367
摘要： The present invention relates to a process for preparing 4,4′-[1-(trifluoromethyl)alkylidene]bis(2,6-diphenylphenols), in particular for preparing 4,4′-[1-(trifluoromethyl)ethylidene]bis(2,6-diphenylphenol), which comprises the self-condensation of cyclohexanone in the presence of a basic catalyst to form tricyclic condensation products, dehydrogenation of the resulting tricyclic condensation products in the presence of a supported transition metal catalyst in the condensed phase to form 2,6-diphenylphenol and reaction of the 2,6-diphenylphenol with a trifluoromethyl ketone. The invention further provides an improved process for preparing 2,6-diphenylphenol by aldol self-condensation of cyclohexanone.
摘要翻译：本发明涉及一种制备4,4' - [1-（三氟甲基）亚烷基]双（2,6-二苯基苯酚）的方法，特别是制备4,4' - [1-（三氟甲基）亚乙基]双（ 2,6-二苯基苯酚），其包括环己酮在碱性催化剂存在下的自缩合以形成三环缩合产物，所得三环缩合产物在冷凝相中负载的过渡金属催化剂存在下脱氢形成 2,6-二苯基苯酚和2,6-二苯基苯酚与三氟甲基酮的反应。本发明还提供了通过环己酮的醛醇自缩合制备2,6-二苯基苯酚的改进方法。

7. 发明授权

US08212084B2 Method for the production of 4,4′-[1-trifluoromethyl)alkylidene]-bis-(2,6-diphenylphenols) 有权
标题翻译：制备4,4' - [1-三氟甲基）亚烷基] - 双（2,6-二苯基苯酚）
公开(公告)号：US08212084B2
公开(公告)日：2012-07-03
申请号：US12808865
申请日：2008-12-17
申请人： Gabriele Gralla , Gunnar Heydrich , Klaus Ebel , Wolfgang Krause
发明人： Gabriele Gralla , Gunnar Heydrich , Klaus Ebel , Wolfgang Krause
IPC分类号： C07C39/16 , C07C39/12
CPC分类号： C07C45/74 , C07C37/07 , C07C37/20 , C07C37/62 , C07C49/613 , C07C49/653 , C07C39/15 , C07C39/367
摘要： The present invention relates to a process for preparing 4,4′-[1-(trifluoromethyl)alkylidene]bis(2,6-diphenylphenols), in particular for preparing 4,4′-[1-(trifluoromethyl)ethylidene]bis(2,6-diphenylphenol), which comprises the self-condensation of cyclohexanone in the presence of a basic catalyst to form tricyclic condensation products, dehydrogenation of the resulting tricyclic condensation products in the presence of a supported transition metal catalyst in the condensed phase to form 2,6-diphenylphenol and reaction of the 2,6-diphenylphenol with a trifluoromethyl ketone. The invention further provides an improved process for preparing 2,6-diphenylphenol by aldol self-condensation of cyclohexanone.
摘要翻译：本发明涉及一种制备4,4' - [1-（三氟甲基）亚烷基]双（2,6-二苯基苯酚）的方法，特别是制备4,4' - [1-（三氟甲基）亚乙基]双（ 2,6-二苯基苯酚），其包括环己酮在碱性催化剂存在下的自缩合以形成三环缩合产物，所得三环缩合产物在冷凝相中负载的过渡金属催化剂存在下脱氢形成 2,6-二苯基苯酚和2,6-二苯基苯酚与三氟甲基酮的反应。本发明还提供了通过环己酮的醛醇自缩合制备2,6-二苯基苯酚的改进方法。

8. 发明授权

US08003829B2 Recovery of phenol ligands during the production of isopulegol 有权
标题翻译：在异丙醇的生产过程中苯酚配体的回收
公开(公告)号：US08003829B2
公开(公告)日：2011-08-23
申请号：US12439325
申请日：2007-08-31
申请人： Gunnar Heydrich , Gabriele Gralla , Klaus Ebel , Marko Friedrich
发明人： Gunnar Heydrich , Gabriele Gralla , Klaus Ebel , Marko Friedrich
IPC分类号： C07C35/08 , C07C35/12 , C07C29/80
CPC分类号： C07C29/80 , B01J31/0214 , B01J31/143 , B01J31/4015 , C07B2200/07 , C07C29/172 , C07C29/56 , C07C35/12 , C07C35/17 , C07C2601/14 , Y02P20/584
摘要： The present invention relates to a method of working up an aluminum-containing reaction product from the production of isopulegol by cyclization of citronellal in the presence of complex compounds, comprising at least one ligand of the formula (I), where R1, R2, R3 are chosen from hydrogen, halogen, nitro, C1-C8-alkyl, C1-C8-alkoxy, di(C1-C4-alkyl)amino and aryl; R4, R5 are chosen from halogen, nitro, C1-C8-alkyl, C1-C8-alkoxy, di(C1-C4-alkyl)amino, aryl or heteroaryl; in which a) the reaction product is subjected to distillative separation to obtain an isopulegol-enriched top product and an isopulegol-depleted bottom product and b) the ligand of the formula (I) is separated off from the bottom product. Moreover, the invention relates to a method of producing isopulegol, and to a method of producing menthol.
摘要翻译：本发明涉及一种通过在复合化合物存在下环绕香茅醛来制备含铝反应产物的方法，所述复合化合物包含至少一种式（I）的配体，其中R1，R2，R3 选自氢，卤素，硝基，C 1 -C 8 - 烷基，C 1 -C 8 - 烷氧基，二（C 1 -C 4 - 烷基）氨基和芳基; R4，R5选自卤素，硝基，C1-C8-烷基，C1-C8-烷氧基，二（C1-C4-烷基）氨基，芳基或杂芳基; 其中a）将反应产物进行蒸馏分离，以获得富含异头翁醇的顶部产物和异胡列胆素的底部产物，和b）将式（I）的配体与底部产物分离。此外，本发明涉及一种生产异胡母醇的方法和一种制备薄荷醇的方法。

9. 发明授权

US08134034B2 Recovery of bis(diarylphenol) ligands during the production of isopulegol 有权
标题翻译：在异高粱生产期间回收双（二芳基苯酚）配体
公开(公告)号：US08134034B2
公开(公告)日：2012-03-13
申请号：US12439270
申请日：2007-08-31
申请人： Gunnar Heydrich , Gabriele Gralla , Klaus Ebel
发明人： Gunnar Heydrich , Gabriele Gralla , Klaus Ebel
IPC分类号： C07C35/08 , C07C35/12 , C07C29/80
CPC分类号： C07C29/56 , B01J31/0214 , B01J31/143 , B01J31/4015 , B01J2531/31 , C07B2200/07 , C07C29/172 , C07C29/80 , C07C2601/14 , Y02P20/584 , C07C35/12 , C07C35/17
摘要： The present invention relates to a method of working up an aluminium-containing reaction product from the production of isopulegol by cyclization of citronellal in the presence of complex compounds, comprising at least one ligand of the formula (I), where Ar1, Ar2, Ar3, Ar4 are chosen from C6-C15-aryl or C2-C15-hetero; R1, R2, R3, R4 are chosen from H, C1-C6-alkyl, C1-C6-perfluoroalkyl, C1-C6-alkoxy, C7-C12-aralkyl, halogen, SiR5bR6bR7b, C6-C10-aryl, NR8bR9b, SR10b, NO2; and where R1 or R2 and/or R3 or R4, together with A, can form an aromatic or nonaromatic cycle; etc.; in which a) the aluminum-containing reaction product is subjected to distillative separation, b) the isopulegol-depleted bottom product is brought into close contact with an aqueous base and c) the ligand of the formula (I) is separated off from the organic phase, preferably by crystallization. Moreover, the invention relates to a method of producing isopulegol, and to a method of producing menthol.
摘要翻译：本发明涉及一种通过在络合物存在下使香茅醛环化制备异胡醇的方法，所述复合化合物包含至少一种式（I）的配位体，其中Ar 1，Ar 2，Ar 3 ，Ar 4选自C 6 -C 15 - 芳基或C 2 -C 15 - 杂原子; R1，R2，R3，R4选自H，C1-C6-烷基，C1-C6-全氟烷基，C1-C6-烷氧基，C7-C12-芳烷基，卤素，SiR5bR6bR7b，C6-C10-芳基，NR8bR9b，SR10b， NO2; 并且其中R 1或R 2和/或R 3或R 4与A一起可以形成芳族或非芳族化合物; 等等。; 其中a）使含铝反应产物进行蒸馏分离，b）将异底三醇消耗的底部产物与碱水溶液紧密接触，并且c）将式（I）的配体与有机物分离出来相，优选通过结晶。此外，本发明涉及一种生产异胡母醇的方法和一种制备薄荷醇的方法。

10. 发明授权

US07960593B2 Process for preparation of menthol by hydrogenation of isopulegol 有权
标题翻译：通过异丙醇氢化制备薄荷醇的方法
公开(公告)号：US07960593B2
公开(公告)日：2011-06-14
申请号：US12670328
申请日：2008-07-16
申请人： Gabriele Gralla , Gunnar Heydrich , Eike Johannes Bergner , Klaus Ebel
发明人： Gabriele Gralla , Gunnar Heydrich , Eike Johannes Bergner , Klaus Ebel
IPC分类号： C07C29/00 , C07C35/12
CPC分类号： C07C29/172 , C07B2200/07 , C07C2601/14 , C07C35/12
摘要： The present invention relates to a process for preparing racemic or optically active menthol by catalytically hydrogenating racemic or optically active isopulegol in the presence of hydrogen and catalysts which comprise nickel-, copper-, zirconium- and molybdenum-containing compounds. The present invention relates specifically to a corresponding process far continuously catalytically hydrogenating L-isopulegol to L-menthol.
摘要翻译：本发明涉及一种通过在氢气存在下催化氢化外消旋或光学活性异胡胆醇来制备外消旋或光学活性薄荷醇的方法和包含含镍，铜，锆和钼的化合物的催化剂。本发明具体涉及将L-异胡胆醇连续催化氢化成L-薄荷醇的相应方法。

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