公开(公告)号：US07777081B2

公开(公告)日：2010-08-17

申请号：US12299980

申请日：2007-05-08

申请人： Mitsuharu Kitamura ,  Junya Nishiuchi ,  Norio Fushimi

发明人： Mitsuharu Kitamura ,  Junya Nishiuchi ,  Norio Fushimi

IPC分类号： C07C47/54 ,  C07C45/49

CPC分类号： C07C5/2246 ,  C07B2200/07 ,  C07C45/49 ,  C07C45/67 ,  C07C45/82 ,  C07C45/83 ,  C07C45/85 ,  C07C47/546 ,  C07C2527/1206 ,  C07C2527/1213 ,  C07C2601/14 ,  C07C13/28

摘要： A process for effectively producing a 4-(4-alkylcyclohexyl)benzaldehyde, 4-(cyclohexyl)benzaldehyde, a 4-(trans-4-alkylcyclohexyl)benzaldehyde and a (trans-4-alkylcyclohexyl)benzene useful for electronic material applications such as liquid crystals and for pharmaceutical and agrochemical applications, etc., are disclosed. The present invention provides (1) a process for producing a 4-(4-alkylcyclohexyl)benzaldehyde or 4-(cyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene or cyclohexylbenzene with carbon monoxide, (2) a process for producing a 4-(trans-4-alkylcyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene having a cis/trans molar ratio of 0.3 or less with carbon monoxide, and (3) a process for producing a (trans-4-alkylcyclohexyl)benzene by isomerizing a mixture of the cis and trans isomers of a (4-alkylcyclohexyl)benzene, all of the processes being performed in the presence of HF and BF3.

摘要翻译： 用于电子材料应用的4-（4-烷基环己基）苯甲醛，4-（环己基）苯甲醛，4-（反-4-烷基环己基）苯甲醛和（反式-4-烷基环己基）苯的方法， 液晶，药用和农用化学品等。 本发明提供（1）通过用一氧化碳使（4-烷基环己基）苯或环己基苯甲酰化制备4-（4-烷基环己基）苯甲醛或4-（环己基）苯甲醛的方法，（2） 通过将顺式/反式摩尔比为0.3以下的（4-烷基环己基）苯与一氧化碳甲酰化，得到4-（反-4-烷基环己基）苯甲醛，（3）制备（反式-4-烷基环己基）苯甲醛的方法， 苯通过使（4-烷基环己基）苯的顺式和反式异构体的混合物异构化，所有方法都在HF和BF 3存在下进行。

公开(公告)号：US20090118547A1

公开(公告)日：2009-05-07

申请号：US12299980

申请日：2007-05-08

申请人： Mitsuharu Kitamura ,  Junya Nishiuchi ,  Norio Fushimi

发明人： Mitsuharu Kitamura ,  Junya Nishiuchi ,  Norio Fushimi

IPC分类号： C07C47/546 ,  C07C45/49

CPC分类号： C07C5/2246 ,  C07B2200/07 ,  C07C45/49 ,  C07C45/67 ,  C07C45/82 ,  C07C45/83 ,  C07C45/85 ,  C07C47/546 ,  C07C2527/1206 ,  C07C2527/1213 ,  C07C2601/14 ,  C07C13/28

摘要： A process for effectively producing a 4-(4-alkylcyclohexyl)benzaldehyde, 4-(cyclohexyl)benzaldehyde, a 4-(trans-4-alkylcyclohexyl)benzaldehyde and a (trans-4-alkylcyclohexyl)benzene useful for electronic material applications such as liquid crystals and for pharmaceutical and agrochemical applications, etc., are disclosed. The present invention provides (1) a process for producing a 4-(4-alkylcyclohexyl)benzaldehyde or 4-(cyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene or cyclohexylbenzene with carbon monoxide, (2) a process for producing a 4-(trans-4-alkylcyclohexyl)benzaldehyde by formylating a (4-alkylcyclohexyl)benzene having a cis/trans molar ratio of 0.3 or less with carbon monoxide, and (3) a process for producing a (trans-4-alkylcyclohexyl)benzene by isomerizing a mixture of the cis and trans isomers of a (4-alkylcyclohexyl)benzene, all of the processes being performed in the presence of HF and BF3.

摘要翻译： 用于电子材料应用的4-（4-烷基环己基）苯甲醛，4-（环己基）苯甲醛，4-（反-4-烷基环己基）苯甲醛和（反式-4-烷基环己基）苯的方法， 液晶，药用和农用化学品等。 本发明提供（1）通过用一氧化碳使（4-烷基环己基）苯或环己基苯甲酰化制备4-（4-烷基环己基）苯甲醛或4-（环己基）苯甲醛的方法，（2） 通过将顺式/反式摩尔比为0.3以下的（4-烷基环己基）苯与一氧化碳甲酰化，得到4-（反-4-烷基环己基）苯甲醛，（3）制备（反式-4-烷基环己基）苯甲醛的方法， 苯通过使（4-烷基环己基）苯的顺式和反式异构体的混合物异构化，所有方法都在HF和BF 3存在下进行。

公开(公告)号：US20050187403A1

公开(公告)日：2005-08-25

申请号：US11063970

申请日：2005-02-24

申请人： Hiroshi Ogawa ,  Junya Nishiuchi ,  Mitsuharu Kitamura ,  Kinji Kato

发明人： Hiroshi Ogawa ,  Junya Nishiuchi ,  Mitsuharu Kitamura ,  Kinji Kato

IPC分类号： C07C51/255 ,  C07C51/265 ,  C07C63/38

CPC分类号： C07C51/265 ,  C07C63/38

摘要： 1,3-Naphthalenedicarboxylic acid is produced by oxidizing 1,3-dialkylnaphthalene in a liquid-phase with an oxygen-containing gas in the presence of a C2-C6 lower aliphatic carboxylic acid solvent and a catalyst comprising a heavy metal and a bromine compound. By regulating the ratio of the total number of bromine atoms fed into a reaction system to the total number of 1,3-dialkylnaphthalene molecules fed into the reaction system within a specific range, 1,3-naphthalenedicarboxylic acid is efficiently produced with low costs. Using 1,3-dimethylnaphthalene, as the starting 1,3-dialkylnaphthalene, which is produced by isomerizing dimethylnaphthalenes in a liquid phase in the presence of a catalyst comprising hydrogen fluoride and boron trifluoride together with a C5-C10 alicyclic saturated hydrocarbon having a five-membered or six-membered ring structure, a highly pure 1,3-naphthalenedicarboxylic acid is efficiently produced.

摘要翻译： 1,3-二萘基二羧酸是通过在C 2 -C 6 -C 6的存在下用含氧气体在液相中氧化1,3-二烷基萘而制备的， 低级脂族羧酸溶剂和包含重金属和溴化合物的催化剂。 通过调节进料到反应体系中的溴原子总量与进料到反应体系中的1,3-二烷基萘分子的总数在特定范围内的比例，可以低成本有效地制备1,3-萘二羧酸。 使用1,3-二甲基萘作为起始1,3-二烷基萘，其通过在包含氟化氢和三氟化硼的催化剂存在下在液相中异构化二甲基萘一起制备，与C 5 N 5 具有5元或6元环结构的-C 10脂肪族饱和烃，高纯度的1,3-萘二羧酸。

公开(公告)号：US08507727B2

公开(公告)日：2013-08-13

申请号：US13496569

申请日：2010-09-16

申请人： Junya Nishiuchi

发明人： Junya Nishiuchi

IPC分类号： C07C45/62

CPC分类号： C07C45/62 ,  C07C49/303 ,  C07C49/337 ,  C07C49/313

摘要： Provided is an industrially superior method for producing cyclohexyl alkyl ketones, which solves the problems in process reduction and in disposal of wastes such as metals.An aromatic ketone represented by a formula (1) is nuclear-hydrogenated with pressurized hydrogen and in the presence of a solvent at a temperature of from 20 to 120° C., in the presence of a catalyst that carries from 0.1 to 20% by weight of a ruthenium atom on the carrier, thereby producing a cyclohexyl alkyl ketone represented by a formula (2): provided that, in the formula (2), n indicates an integer of from 1 to 3; R represents a hydroxyl group, a cyclohexyl group, an alkyl group having from 1 to 4 carbon atoms, or an acyl group having from 1 to 4 carbon atoms

摘要翻译： 提供了一种工业上优异的环己基烷基酮的制备方法，其解决了工艺的还原和金属等废弃物的处理中的问题。 由式（1）表示的芳族酮在加压氢气下，在溶剂存在下，在20〜120℃的温度下，在催化剂存在下，在0.1〜20％ 载体上的钌原子的重量，由此制备由式（2）表示的环己基烷基酮：条件是在式（2）中，n表示1至3的整数; R表示羟基，环己基，具有1至4个碳原子的烷基或具有1至4个碳原子的酰基

公开(公告)号：US20120178970A1

公开(公告)日：2012-07-12

申请号：US13496569

申请日：2010-09-16

申请人： Junya Nishiuchi

发明人： Junya Nishiuchi

IPC分类号： C07C45/62

CPC分类号： C07C45/62 ,  C07C49/303 ,  C07C49/337 ,  C07C49/313

摘要： Provided is an industrially superior method for producing cyclohexyl alkyl ketones, which solves the problems in process reduction and in disposal of wastes such as metals.An aromatic ketone represented by a formula (1) is nuclear-hydrogenated with pressurized hydrogen and in the presence of a solvent at a temperature of from 20 to 120° C., in the presence of a catalyst that carries from 0.1 to 20% by weight of a ruthenium atom on the carrier, thereby producing a cyclohexyl alkyl ketone represented by a formula (2): provided that, in the formula (2), n indicates an integer of from 1 to 3; R represents a hydroxyl group, a cyclohexyl group, an alkyl group having from 1 to 4 carbon atoms, or an acyl group having from 1 to 4 carbon atoms

摘要翻译： 提供了一种工业上优异的环己基烷基酮的制备方法，其解决了工艺的还原和金属等废弃物的处理中的问题。 由式（1）表示的芳族酮在加压氢气下，在溶剂存在下，在20〜120℃的温度下，在催化剂存在下，在0.1〜20％ 载体上的钌原子的重量，由此制备由式（2）表示的环己基烷基酮：条件是在式（2）中，n表示1至3的整数; R表示羟基，环己基，具有1至4个碳原子的烷基或具有1至4个碳原子的酰基

公开(公告)号：US08168819B2

公开(公告)日：2012-05-01

申请号：US12295761

申请日：2007-04-04

申请人： Junya Nishiuchi

发明人： Junya Nishiuchi

IPC分类号： C07C51/255

CPC分类号： C07C2/70 ,  C07C51/265 ,  C07C2521/18 ,  C07C2523/42 ,  C07C2523/44 ,  C07C2527/1206 ,  C07C2527/1213 ,  C07C2601/14 ,  Y02P20/52 ,  Y02P20/584 ,  C07C13/28 ,  C07C63/331

摘要： The present invention provides an industrially advantageous process for producing 5-phenylisophthalic acid, which process attains excellent selectivity and yield and also realizes recovery and reuse of a catalyst.The process for producing 5-phenylisophthalic acid represented by formula (1) is characterized in that the process includes the following steps (A) to (C): (A) reacting m-xylene with cyclohexene in the presence of hydrogen fluoride and boron trifluoride, to thereby produce 1-cyclohexyl-3,5-dimethylbenzene; (B) dehydrogenating the 1-cyclohexyl-3,5-dimethylbenzene produced in step (A) in the presence of a dehydrogenation catalyst, to thereby produce 3,5-dimethylbiphenyl; and (C) dissolving the 3,5-dimethylbiphenyl produced in step (B) in a solvent and oxidizing the 3,5-dimethylbiphenyl in the co-presence of an oxidation catalyst, to thereby produce 5-phenylisophthalic acid.

摘要翻译： 本发明提供了一种工业上有利的5-苯基间苯二甲酸的制备方法，该方法获得优异的选择性和收率，并且还实现了催化剂的回收和再利用。 由式（1）表示的5-苯基间苯二甲酸的制备方法的特征在于该方法包括以下步骤（A）至（C）：（A）在氟化氢和三氟化硼存在下使间二甲苯与环己烯反应 从而制备1-环己基-3,5-二甲基苯; （B）在脱氢催化剂存在下使步骤（A）中生成的1-环己基-3,5-二甲基苯脱氢，由此制得3,5-二甲基联苯; 和（C）将步骤（B）中制备的3,5-二甲基联苯溶解在溶剂中并在氧化催化剂的共存下氧化3,5-二甲基联苯，从而产生5-苯基间苯二甲酸。

公开(公告)号：US20090299111A1

公开(公告)日：2009-12-03

申请号：US11996147

申请日：2006-07-25

申请人： Yutaka Kanbara ,  Kenji Morohashi ,  Junya Nishiuchi

发明人： Yutaka Kanbara ,  Kenji Morohashi ,  Junya Nishiuchi

IPC分类号： C07C15/12

CPC分类号： C07C2/862 ,  B01J23/26 ,  B01J23/464 ,  B01J29/18 ,  B01J29/85 ,  C07C13/19

摘要： The invention provides a method for producing an (alkylphenyl)alkylcyclohexane, including a step of condensing an alkylbenzene with an alkylcyclohexene or an alkylcyclohexanol in the presence of an acid catalyst, and (alkylphenyl)alkylcyclohexane represented by formula (8). The (alkylphenyl)alkylcyclohexane produced through the production method can be transformed into an alkylbiphenyl, a biphenylpolycarboxylic acid, or a biphenylpolycarboxylic anhydride. Through the production method, an (alkylphenyl)alkylcyclohexane and an alkylbiphenyl of interest can be readily and selectively produced. (wherein R1 represents a C1-C4 alkyl group; R2 represents a C1-C4 alkyl group; m is an integer of 0 to 2; n′ is an integer of 2 to 5; other conditions are the same as defined in claim 18.)

摘要翻译： 本发明提供一种（烷基苯基）烷基环己烷的制备方法，包括在酸催化剂存在下使烷基苯与烷基环己烯或烷基环己醇缩合的步骤，和由式（8）表示的（烷基苯基）烷基环己烷。 通过制备方法生产的（烷基苯基）烷基环己烷可以转化成烷基联苯，联苯多羧酸或联苯多羧酸酐。 通过该制造方法，可以容易且选择性地制备（烷基苯基）烷基环己烷和感兴趣的烷基联苯。 （其中R1表示C1-C4烷基; R2表示C1-C4烷基; m为0〜2的整数; n'为2〜5的整数，其他条件与权利要求18所述相同。 ）

公开(公告)号：US20090156858A1

公开(公告)日：2009-06-18

申请号：US12295761

申请日：2007-04-04

申请人： Junya Nishiuchi

发明人： Junya Nishiuchi

IPC分类号： C07C51/16

CPC分类号： C07C2/70 ,  C07C51/265 ,  C07C2521/18 ,  C07C2523/42 ,  C07C2523/44 ,  C07C2527/1206 ,  C07C2527/1213 ,  C07C2601/14 ,  Y02P20/52 ,  Y02P20/584 ,  C07C13/28 ,  C07C63/331

摘要： The present invention provides an industrially advantageous process for producing 5-phenylisophthalic acid, which process attains excellent selectivity and yield and also realizes recovery and reuse of a catalyst.The process for producing 5-phenylisophthalic acid represented by formula (1) is characterized in that the process includes the following steps (A) to (C): (A) reacting m-xylene with cyclohexene in the presence of hydrogen fluoride and boron trifluoride, to thereby produce 1-cyclohexyl-3,5-dimethylbenzene; (B) dehydrogenating the 1-cyclohexyl-3,5-dimethylbenzene produced in step (A) in the presence of a dehydrogenation catalyst, to thereby produce 3,5-dimethylbiphenyl; and (C) dissolving the 3,5-dimethylbiphenyl produced in step (B) in a solvent and oxidizing the 3,5-dimethylbiphenyl in the co-presence of an oxidation catalyst, to thereby produce 5-phenylisophthalic acid.

摘要翻译： 本发明提供了一种工业上有利的5-苯基间苯二甲酸的制备方法，该方法获得优异的选择性和收率，并且还实现了催化剂的回收和再利用。 由式（1）表示的5-苯基间苯二甲酸的制备方法的特征在于该方法包括以下步骤（A）至（C）：（A）在氟化氢和三氟化硼存在下使间二甲苯与环己烯反应 从而制备1-环己基-3,5-二甲基苯; （B）在脱氢催化剂存在下使步骤（A）中生成的1-环己基-3,5-二甲基苯脱氢，由此制得3,5-二甲基联苯; 和（C）将步骤（B）中制备的3,5-二甲基联苯溶解在溶剂中并在氧化催化剂的共存下氧化3,5-二甲基联苯，从而产生5-苯基间苯二甲酸。

公开(公告)号：US07241925B2

公开(公告)日：2007-07-10

申请号：US11011136

申请日：2004-12-15

申请人： Kinji Kato ,  Junya Nishiuchi ,  Mitsuharu Kitamura

发明人： Kinji Kato ,  Junya Nishiuchi ,  Mitsuharu Kitamura

IPC分类号： C07C45/49

CPC分类号： C07C45/49 ,  C07C47/55

摘要： In the production method of the invention, a halogen-substituted aromatic compound is reacted with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride into a corresponding halogen-substituted aromatic aldehyde. By the use of hydrogen fluoride and boron trifluoride, the para position to halogen atom is selectively formylated to provide the halogen-substituted aromatic aldehyde in high yields in a short reaction time even at temperatures lower than room temperature.

摘要翻译： 在本发明的制造方法中，将卤素取代的芳香族化合物与一氧化碳在氟化氢和三氟化硼的存在下反应成相应的卤素取代的芳香醛。 通过使用氟化氢和三氟化硼，对卤素原子的对位选择性甲酰化，即使在低于室温的温度下，也可以在短的反应时间内以高产率提供卤素取代的芳族醛。

公开(公告)号：US20050143605A1

公开(公告)日：2005-06-30

申请号：US11011136

申请日：2004-12-15

申请人： Kinji Kato ,  Junya Nishiuchi ,  Mitsuharu Kitamura

发明人： Kinji Kato ,  Junya Nishiuchi ,  Mitsuharu Kitamura

IPC分类号： C07C45/49

CPC分类号： C07C45/49 ,  C07C47/55

摘要： In the production method of the invention, a halogen-substituted aromatic compound is reacted with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride into a corresponding halogen-substituted aromatic aldehyde. By the use of hydrogen fluoride and boron trifluoride, the para position to halogen atom is selectively formylated to provide the halogen-substituted aromatic aldehyde in high yields in a short reaction time even at temperatures lower than room temperature.

摘要翻译： 在本发明的制造方法中，将卤素取代的芳香族化合物与一氧化碳在氟化氢和三氟化硼的存在下反应成相应的卤素取代的芳香醛。 通过使用氟化氢和三氟化硼，对卤素原子的对位选择性甲酰化，即使在低于室温的温度下，也可以在短的反应时间内以高产率提供卤素取代的芳族醛。