公开(公告)号：US09024070B2

公开(公告)日：2015-05-05

申请号：US13980641

申请日：2012-01-30

申请人： Tatsuyuki Kumano ,  Yukiya Ibi ,  Kuniaki Arasuna ,  Shinichi Nagao

发明人： Tatsuyuki Kumano ,  Yukiya Ibi ,  Kuniaki Arasuna ,  Shinichi Nagao

IPC分类号： C07C211/00 ,  C07C209/48 ,  B01J23/22 ,  B01J23/26 ,  B01J37/00 ,  B01J23/00 ,  B01J23/75 ,  B01J23/755

CPC分类号： C07C209/48 ,  B01J23/002 ,  B01J23/22 ,  B01J23/26 ,  B01J23/75 ,  B01J23/755 ,  B01J37/0045 ,  B01J2523/00 ,  C07C211/27 ,  B01J2523/12 ,  B01J2523/13 ,  B01J2523/305 ,  B01J2523/51 ,  B01J2523/55 ,  B01J2523/67 ,  B01J2523/68

摘要： Provided is a method for stably and economically producing xylylenediamine with a high yield and long catalyst service life by hydrogenating dicyanobenzene that is obtained by ammoxidating xylene. By bringing an aqueous basic solution into contact with a dicyanobenzene-absorbed liquid, which is obtained by bringing an ammoxidation reaction gas into contact with an organic solvent, under specified temperature conditions, and subjecting a base and a carboxylic acid in the dicyanobenzene-absorbed liquid to a neutralization reaction so as to form an aqueous phase that contains a water-soluble salt, and then subjecting an organic phase and the aqueous phase to liquid-liquid separation so as to remove the aqueous phase, it is possible to remove the carboxylic acid contained in the dicyanobenzene-absorbed liquid with high selectivity while inhibiting loss of the dicyanobenzene. By subjecting the raw material dicyanobenzene, which is obtained by separating low boiling point compounds from the post liquid-liquid separation organic phase by distillation under reduced pressure, to hydrogenation, xylylenediamine is produced with a high yield and the service life of the hydrogenation catalyst is extended.

摘要翻译： 本发明提供一种通过氢化二甲苯得到的二氰基苯来稳定和经济地制备苯二甲胺的方法，其产率高，催化剂使用寿命长。 通过使碱性水溶液与规定的温度条件下使氨氧化反应气体与有机溶剂接触而获得的二氰基苯吸收液接触，并将二羧酸吸收液中的碱和羧酸 进行中和反应，形成含有水溶性盐的水相，然后使有机相和水相进行液 - 液分离以除去水相，可以除去羧酸 包含在二氰基苯吸收液体中，同时抑制二氰基苯的损失。 通过将来自后液 - 液分离有机相的低沸点化合物通过减压蒸馏分离得到的原料二氰基苯进行氢化，以高产率生产苯二甲胺，氢化催化剂的使用寿命为 延长

公开(公告)号：US20130296609A1

公开(公告)日：2013-11-07

申请号：US13980641

申请日：2012-01-30

申请人： Tatsuyuki Kumano ,  Yukiya Ibi ,  Kuniaki Arasuna ,  Shinichi Nagao

发明人： Tatsuyuki Kumano ,  Yukiya Ibi ,  Kuniaki Arasuna ,  Shinichi Nagao

IPC分类号： C07C209/48

CPC分类号： C07C209/48 ,  B01J23/002 ,  B01J23/22 ,  B01J23/26 ,  B01J23/75 ,  B01J23/755 ,  B01J37/0045 ,  B01J2523/00 ,  C07C211/27 ,  B01J2523/12 ,  B01J2523/13 ,  B01J2523/305 ,  B01J2523/51 ,  B01J2523/55 ,  B01J2523/67 ,  B01J2523/68

摘要： Provided is a method for stably and economically producing xylylenediamine with a high yield and long catalyst service life by hydrogenating dicyanobenzene that is obtained by ammoxidating xylene. By bringing an aqueous basic solution into contact with a dicyanobenzene-absorbed liquid, which is obtained by bringing an ammoxidation reaction gas into contact with an organic solvent, under specified temperature conditions, and subjecting a base and a carboxylic acid in the dicyanobenzene-absorbed liquid to a neutralization reaction so as to form an aqueous phase that contains a water-soluble salt, and then subjecting an organic phase and the aqueous phase to liquid-liquid separation so as to remove the aqueous phase, it is possible to remove the carboxylic acid contained in the dicyanobenzene-absorbed liquid with high selectivity while inhibiting loss of the dicyanobenzene. By subjecting the raw material dicyanobenzene, which is obtained by separating low boiling point compounds from the post liquid-liquid separation organic phase by distillation under reduced pressure, to hydrogenation, xylylenediamine is produced with a high yield and the service life of the hydrogenation catalyst is extended.

摘要翻译： 本发明提供一种通过氢化二甲苯得到的二氰基苯来稳定和经济地制备苯二甲胺的方法，其产率高，催化剂使用寿命长。 通过使碱性水溶液与规定的温度条件下使氨氧化反应气体与有机溶剂接触而获得的二氰基苯吸收液接触，并将二羧酸吸收液中的碱和羧酸 进行中和反应，形成含有水溶性盐的水相，然后使有机相和水相进行液 - 液分离以除去水相，可以除去羧酸 包含在二氰基苯吸收液体中，同时抑制二氰基苯的损失。 通过将来自后液 - 液分离有机相的低沸点化合物通过减压蒸馏分离得到的原料二氰基苯进行氢化，以高产率生产苯二甲胺，氢化催化剂的使用寿命为 延长

公开(公告)号：US08212080B2

公开(公告)日：2012-07-03

申请号：US12633223

申请日：2009-12-08

申请人： Tatsuyuki Kumano ,  Kenji Nakaya ,  Shinichi Nagao

发明人： Tatsuyuki Kumano ,  Kenji Nakaya ,  Shinichi Nagao

IPC分类号： C07C209/00 ,  C07C211/00

CPC分类号： C07C211/27 ,  C07C209/48

摘要： A method of producing xylylenediamine by the hydrogenation of dicyanobenzene obtained by the ammoxidation of xylene in a high yield while prolonging the catalyst life. In the method, a molten dicyanobenzene from which compounds having a boiling point lower than that of dicyanobenzene have been removed but compounds having a boiling point higher than that of dicyanobenzene are not removed is dissolved in a solvent containing liquid ammonia. By this dissolution, at least part of dicyanobenzene polymers precipitates as insolubles. The precipitates are removed by a solid-liquid separation. By subjecting the resulting solution containing the dicyanobenzene polymers in a reduced amount to hydrogenation, xylylenediamine is produced in a high yield and the life time of hydrogenation catalyst is prolonged.

摘要翻译： 通过二甲苯氨氧化得到的二氰基苯加氢制备苯二甲胺的方法，同时延长了催化剂的使用寿命。 在该方法中，除去沸点低于二氰基苯的化合物的熔融二氰基苯，但没有除去沸点高于二氰基苯的沸点的化合物溶解在含有液氨的溶剂中。 通过这种溶解，至少部分二氰基苯聚合物作为不溶物沉淀。 通过固液分离除去沉淀物。 通过将含有二氰基苯聚合物的所得溶液以减少的量进行氢化，以高产率生产苯二甲胺，延长氢化催化剂的使用寿命。

公开(公告)号：US20100168474A1

公开(公告)日：2010-07-01

申请号：US12633223

申请日：2009-12-08

申请人： Tatsuyuki KUMANO ,  Kenji Nakaya ,  Shinichi Nagao

发明人： Tatsuyuki KUMANO ,  Kenji Nakaya ,  Shinichi Nagao

IPC分类号： C07C211/43

CPC分类号： C07C211/27 ,  C07C209/48

摘要： A method of producing xylylenediamine by the hydrogenation of dicyanobenzene obtained by the ammoxidation of xylene in a high yield while prolonging the catalyst life. In the method, a molten dicyanobenzene from which compounds having a boiling point lower than that of dicyanobenzene have been removed but compounds having a boiling point higher than that of dicyanobenzene are not removed is dissolved in a solvent containing liquid ammonia. By this dissolution, at least part of dicyanobenzene polymers precipitates as insolubles. The precipitates are removed by a solid-liquid separation. By subjecting the resulting solution containing the dicyanobenzene polymers in a reduced amount to hydrogenation, xylylenediamine is produced in a high yield and the life time of hydrogenation catalyst is prolonged.

摘要翻译： 通过二甲苯氨氧化得到的二氰基苯加氢制备苯二甲胺的方法，同时延长了催化剂的使用寿命。 在该方法中，除去沸点低于二氰基苯的化合物的熔融二氰基苯，但没有除去沸点高于二氰基苯的沸点的化合物溶解在含有液氨的溶剂中。 通过这种溶解，至少部分二氰基苯聚合物作为不溶物沉淀。 通过固液分离除去沉淀物。 通过将含有二氰基苯聚合物的所得溶液以减少的量进行氢化，以高产率生产苯二甲胺，延长氢化催化剂的使用寿命。

公开(公告)号：US07465832B2

公开(公告)日：2008-12-16

申请号：US11749787

申请日：2007-05-17

申请人： Tomohiro Sugawara ,  Takafumi Abe ,  Tatsuyuki Kumano ,  Kinji Kato

发明人： Tomohiro Sugawara ,  Takafumi Abe ,  Tatsuyuki Kumano ,  Kinji Kato

IPC分类号： C07C209/48

CPC分类号： C07C209/48 ,  C07C211/27

摘要： A method of producing xylylenediamine of the present invention includes the steps of: subjecting a liquid mixture of phthalonitriles with liquid ammonia or a mixture of liquid ammonia and an organic solvent to a first catalytic hydrogenation treatment, thereby hydrogenating the phthalonitriles to obtain a reaction product (A), wherein a content of the liquid ammonia or the mixture of liquid ammonia and an organic solvent is 80 wt % or more; removing the liquid ammonia in the reaction product (A) to obtain a reaction product (B); subjecting the reaction product (B) to a second catalytic hydrogenation treatment, thereby hydrogenating cyanobenzylamine to obtain a reaction product (C); and distilling the reaction product (C) to purify xylylenediamine.

摘要翻译： 本发明的苯二甲胺的制造方法包括以下步骤：将液氨或液态氨与有机溶剂的混合液的酞腈液进行第一次催化氢化处理，氢化二氯腈得到反应产物（ A），其中液氨或液氨和有机溶剂的混合物的含量为80重量％以上; 除去反应产物（A）中的液氨，得到反应产物（B）; 使反应产物（B）进行第二催化氢化处理，由此氢化氰基苄胺得到反应产物（C）; 并蒸馏反应产物（C）以净化苯二甲胺。

公开(公告)号：US20070270613A1

公开(公告)日：2007-11-22

申请号：US11749787

申请日：2007-05-17

申请人： Tomohiro Sugawara ,  Takafumi Abe ,  Tatsuyuki Kumano ,  Kinji Kato

发明人： Tomohiro Sugawara ,  Takafumi Abe ,  Tatsuyuki Kumano ,  Kinji Kato

IPC分类号： C07C209/44

CPC分类号： C07C209/48 ,  C07C211/27

摘要： A method of producing xylylenediamine of the present invention includes the steps of: subjecting a liquid mixture of phthalonitriles with liquid ammonia or a mixture of liquid ammonia and an organic solvent to a first catalytic hydrogenation treatment, thereby hydrogenating the phthalonitriles to obtain a reaction product (A), wherein a content of the liquid ammonia or the mixture of liquid ammonia and an organic solvent is 80 wt % or more; removing the liquid ammonia in the reaction product (A) to obtain a reaction product (B); subjecting the reaction product (B) to a second catalytic hydrogenation treatment, thereby hydrogenating cyanobenzylamine to obtain a reaction product (C); and distilling the reaction product (C) to purify xylylenediamine.

摘要翻译： 本发明的苯二甲胺的制造方法包括以下步骤：将液氨或液态氨与有机溶剂的混合液的酞腈液进行第一次催化氢化处理，氢化二氯腈得到反应产物（ A），其中液氨或液氨和有机溶剂的混合物的含量为80重量％以上; 除去反应产物（A）中的液氨，得到反应产物（B）; 使反应产物（B）进行第二催化氢化处理，由此氢化氰基苄胺得到反应产物（C）; 并蒸馏反应产物（C）以净化苯二甲胺。

公开(公告)号：US07626057B2

公开(公告)日：2009-12-01

申请号：US11768949

申请日：2007-06-27

申请人： Tatsuyuki Kumano ,  Ryusuke Shigematsu ,  Kinji Kato ,  Kenji Nakaya

发明人： Tatsuyuki Kumano ,  Ryusuke Shigematsu ,  Kinji Kato ,  Kenji Nakaya

IPC分类号： C07C209/00

CPC分类号： C07C209/48 ,  C07C209/84 ,  C07C211/27

摘要： A method of producing xylylenediamine by a two-stage hydrogenation of a starting phthalonitrile in a solvent. The main steps of the method are a hydrogenation step 1 and a hydrogenation step 2. In the hydrogenation step 1, a solution of the starting phthalonitrile in the solvent containing liquid ammonia is fed to an inlet of a first reaction zone and the hydrogenation is carried out in the first reaction zone in the presence of a heterogeneous catalyst, to hydrogenate nitrile groups in the starting phthalonitrile to aminomethyl groups. A part of the hydrogenation product solution from the first reaction zone is circulated to the inlet of the first reaction zone and the rest is introduced into the hydrogenation step 2 where further undergoes the hydrogenation.

摘要翻译： 通过在溶剂中通过起始邻苯二甲腈的两步氢化制备苯二甲胺的方法。 该方法的主要步骤是氢化步骤1和氢化步骤2.在氢化步骤1中，将起始邻苯二甲腈在含有液氨的溶剂中的溶液进料到第一反应区的入口，并进行氢化 在非均相催化剂存在下在第一反应区中，将起始邻苯二甲腈中的腈基氢化成氨基甲基。 将来自第一反应区的氢化产物溶液的一部分循环到第一反应区的入口，其余部分被引入氢化步骤2中，其中进一步进行氢化。

公开(公告)号：US20080009654A1

公开(公告)日：2008-01-10

申请号：US11768949

申请日：2007-06-27

申请人： Tatsuyuki Kumano ,  Ryusuke Shigematsu ,  Kinji Kato ,  Kenji Nakaya

发明人： Tatsuyuki Kumano ,  Ryusuke Shigematsu ,  Kinji Kato ,  Kenji Nakaya

IPC分类号： C07C209/00

CPC分类号： C07C209/48 ,  C07C209/84 ,  C07C211/27

摘要： A method of producing xylylenediamine by a two-stage hydrogenation of a starting phthalonitrile in a solvent. The main steps of the method are a hydrogenation step 1 and a hydrogenation step 2. In the hydrogenation step 1, a solution of the starting phthalonitrile in the solvent containing liquid ammonia is fed to an inlet of a first reaction zone and the hydrogenation is carried out in the first reaction zone in the presence of a heterogeneous catalyst, to hydrogenate nitrile groups in the starting phthalonitrile to aminomethyl groups. A part of the hydrogenation product solution from the first reaction zone is circulated to the inlet of the first reaction zone and the rest is introduced into the hydrogenation step 2 where further undergoes the hydrogenation.

摘要翻译： 通过在溶剂中通过起始邻苯二甲腈的两步氢化制备苯二甲胺的方法。 该方法的主要步骤是氢化步骤1和氢化步骤2.在氢化步骤1中，将起始邻苯二甲腈在含有液氨的溶剂中的溶液进料到第一反应区的入口，并进行氢化 在非均相催化剂存在下在第一反应区中，将起始邻苯二甲腈中的腈基氢化成氨基甲基。 将来自第一反应区的氢化产物溶液的一部分循环到第一反应区的入口，其余部分被引入氢化步骤2中，其中进一步进行氢化。

公开(公告)号：US07202380B2

公开(公告)日：2007-04-10

申请号：US10755394

申请日：2004-01-13

申请人： Tatsuyuki Kumano ,  Seiji Adachi ,  Hiroshi Ogawa

发明人： Tatsuyuki Kumano ,  Seiji Adachi ,  Hiroshi Ogawa

IPC分类号： C07C51/235

CPC分类号： C07C51/43 ,  C07C51/265 ,  C07C51/56 ,  C07C63/313

摘要： In a method of producing pyromellitic acid by liquid-phase oxidizing 2,4,5-trimethylbenzaldehyde in a water solvent with molecular oxygen, a recrystallization mother liquor separated in a recrystallization step is recycled to the oxidation step after a part of the water solvent is removed. With this method, the loss of pyromellitic acid and the oxidation catalyst can be minimized and the burden of discharging the waste water is reduced without lowering the efficiency of the liquid-phase oxidation reaction.

摘要翻译： 在用分子氧在水溶剂中通过液相氧化2,4,5-三甲基苯甲醛制备均苯四酸的方法中，在一部分水溶剂为重结晶步骤后，将重结晶步骤中分离的再结晶母液循环至氧化步骤 删除。 通过该方法，可以将均苯四酸和氧化催化剂的损失降至最低，并且降低排出废水的负担而不降低液相氧化反应的效率。

公开(公告)号：US08759588B2

公开(公告)日：2014-06-24

申请号：US13062334

申请日：2009-08-27

申请人： Shinichi Nagao ,  Tatsuyuki Kumano ,  Kenji Nakaya ,  Ryusuke Shigematsu ,  Kinji Kato

发明人： Shinichi Nagao ,  Tatsuyuki Kumano ,  Kenji Nakaya ,  Ryusuke Shigematsu ,  Kinji Kato

IPC分类号： C07C209/00

CPC分类号： C07C209/48 ,  C07C211/27

摘要： The invention provides a process for producing xylylenediamine, including supplying a solution of phthalonitrile dissolved in a solvent to a reactor filled with a catalyst and hydrogenating the phthalonitrile to produce xylylenediamine, characterized in that the process includes halting supply of the solution; (2) bringing a washing liquid into contact with the catalyst, the washing liquid having a phthalonitrile content of 3 mass % or less and a xylylenediamine content of 1 mass % or more; and after completion of the contact, resuming supply of the solution, and employing the catalyst continuously in hydrogenation. Through the production process of the invention, the catalyst can be employed continuously for a long period of time, and the catalyst-related cost can be considerably reduced.

摘要翻译： 本发明提供了一种生产苯二甲胺的方法，包括将溶于溶剂中的邻苯二甲腈溶液供应到填充有催化剂的反应器中，并使邻苯二甲腈氢化以产生苯二甲胺，其特征在于该方法包括停止溶液的供应; （2）使洗涤液与催化剂接触，洗涤液的邻苯二腈含量为3质量％以下，苯二甲胺含量为1质量％以上; 接触完成后，恢复溶液的供应，并在催化剂中连续使用催化剂。 通过本发明的制造方法，能够长时间连续使用催化剂，能够显着降低催化剂成本。