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1. 发明申请

US20120116124A1 PROCESS FOR REDUCTIVE AMINATION OF ALIPHATIC CYANOALDEHYDES TO ALIPHATIC DIAMINES 有权
标题翻译：脂肪族二胺的还原胺化方法
公开(公告)号：US20120116124A1
公开(公告)日：2012-05-10
申请号：US13383596
申请日：2010-07-30
申请人： Erich J. Molitor , Erich J. Molitor , Daniel A. Hickman , Shawn D. Feist , David C. Molzahn , Stacie Santhany , Abraham d. Schuitman
发明人： Erich J. Molitor , Erich J. Molitor , Daniel A. Hickman , Shawn D. Feist , David C. Molzahn , Stacie Santhany , Abraham d. Schuitman
IPC分类号： C07C209/48 , C07C211/18
CPC分类号： C07C209/48 , C07C2601/14 , C07C211/18
摘要： The instant invention provides a process for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines, and aliphatic diamines produced via such method. The process for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines comprises the steps of: (1) providing a mixture of one or more cycloaliphatic cyanoaldehydes, optionally water, and optionally one or more solvents, wherein said one or more cycloaliphatic cyanoaldehydes are selected from the group consisting of 1,3-cyanocyclohexane carboxaldehyde, 1,4-cyanocyclohexane carboxaldehyde, mixtures thereof, and combinations thereof; (2) contacting said mixture with a metal carbonate based solid bed or a weak base anion exchange resin bed at a temperature in the range of 15 to 40° C. for a period of at least 1 minute or more, for example 5 minutes or more; (3) thereby treating said mixture, wherein said treated mixture has a pH in the range of 6 to 9; (4) feeding said treated mixture, hydrogen, and ammonia into a continuous reductive amination reactor system; (6) contacting said treated mixture, hydrogen, and ammonia with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature in the range of from 80° C. to about 160° C. and a pressure in the range of from 700 to 3500 psig; (7) thereby producing one or more cycloaliphatic diamines, wherein said one or more cycloaliphatic diamines are diamines selected from the group consisting of 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, combinations thereof, and mixtures thereof.
摘要翻译：本发明提供了脂肪族氰醛还原胺化成脂肪族二胺的方法，以及通过这种方法制备的脂肪族二胺。将脂族氰醛还原胺化成脂族二胺的方法包括以下步骤：（1）提供一种或多种脂环族氰醛，任选的水和任选的一种或多种溶剂的混合物，其中所述一种或多种脂环族氰醛选自由1,3-氰基环己烷甲醛，1,4-氰基环己烷甲醛，其混合物及其组合组成的组; （2）使所述混合物与金属碳酸盐基固体床或弱碱性阴离子交换树脂床在15至40℃的温度下接触至少1分钟或更长的时间，例如5分钟，或更多; （3），从而处理所述混合物，其中所述处理的混合物的pH在6至9的范围内; （4）将所述处理的混合物，氢气和氨进料到连续还原胺化反应器系统中; （6）在一种或多种非均相金属基催化剂体系的存在下，在80℃至约160℃的温度范围内使所述经处理的混合物，氢气和氨彼此接触，并且在范围从700至3500psig; （7），从而产生一种或多种脂环族二胺，其中所述一种或多种脂环族二胺是选自1,3-双（氨基甲基）环己烷，1,4-双（氨基甲基）环己烷及其组合的二胺和其混合物。

2. 发明申请

US20120116122A1 PROCESS FOR THE CONVERSION OF ALIPHATIC CYCLIC AMINES TO ALIPHATIC DIAMINES 有权
标题翻译：脂肪酸环糊精转化成脂肪酸的方法
公开(公告)号：US20120116122A1
公开(公告)日：2012-05-10
申请号：US13383525
申请日：2010-07-30
申请人： Shawn D. Feist , Daniel A. Hickman , Erich J. Molitor , David C. Molzahn , Stacie Santhany , Abraham D. Schuitman
发明人： Shawn D. Feist , Daniel A. Hickman , Erich J. Molitor , David C. Molzahn , Stacie Santhany , Abraham D. Schuitman
IPC分类号： C07C209/62 , C07C211/12 , C07C211/18
CPC分类号： C07C209/62 , C07C211/12 , C07C211/18 , C07C2601/14
摘要： The instant invention is a process for the conversion of aliphatic cyclic amines to aliphatic diamines. The process for conversion of aliphatic cyclic amines to aliphatic diamines comprises the steps of: (1) selecting one or more cyclic amines; (2) contacting said one or more cyclic amines with ammonia and hydrogen, optionally water, and optionally one or more solvents in the presence of one or more heterogeneous metal based catalyst systems at a temperature in the range of from 120° C. to about 250° C. and a pressure in the range of from 700 to 3500 psig for a period in the range of at least one hour or more in one or more reactor systems; (3) forming a product mixture comprising one or more aliphatic diamine, optionally a portion of said one or more cyclic amines, optionally a portion of said ammonia, optionally a portion of said hydrogen, optionally water, and optionally a portion of said one or more solvents; (4) removing said product mixture from the reactor system; (5) removing at least a portion of said portion of ammonia, said portion of hydrogen, or mixture thereof from said product mixture via distillation; (6) removing at least a portion of said portion of water via distillation; (7) removing at least a portion of said portion of one or more optional solvents via distillation; (8) removing at least a portion of said portion of one or more cyclic amines; (9) thereby separating said one or more aliphatic diamines from said product mixture; and (10) thereby converting said one or more cyclic amines to one or more aliphatic diamines.
摘要翻译：本发明是将脂族环胺转化为脂族二胺的方法。将脂族环胺转化为脂肪族二胺的方法包括以下步骤：（1）选择一种或多种环胺; （2）在一种或多种非均相金属基催化剂体系的存在下，在120℃至约20℃的温度下，使所述一种或多种环胺与氨和氢，任选的水，以及任选的一种或多种溶剂接触。 250℃，压力范围为700-300psig，在一个或多个反应器系统中至少1小时以上; （3）形成包含一种或多种脂族二胺，任选地一部分所述一种或多种环胺，任选地一部分所述氨，任选地一部分所述氢，任选的水，以及任选地一部分所述一种或多种更多溶剂; （4）从反应器系统中除去所述产物混合物; （5）通过蒸馏从所述产物混合物中除去所述部分氨，所述部分氢或其混合物的至少一部分; （6）通过蒸馏除去所述部分水的至少一部分; （7）通过蒸馏除去一种或多种任选溶剂的所述部分的至少一部分; （8）除去一种或多种环胺的所述部分的至少一部分; （9），从而将所述一种或多种脂族二胺与所述产物混合物分离; 和（10），从而将所述一种或多种环胺转化为一种或多种脂族二胺。

3. 发明授权

US09035098B2 Process for the conversion of aliphatic cyclic amines to aliphatic diamines 有权
标题翻译：将脂族环胺转化为脂族二胺的方法
公开(公告)号：US09035098B2
公开(公告)日：2015-05-19
申请号：US13383525
申请日：2010-07-30
申请人： Shawn D. Feist , Daniel A. Hickman , Erich J. Molitor , David C. Molzahn , Stacie Santhany , Abraham D. Schuitman
发明人： Shawn D. Feist , Daniel A. Hickman , Erich J. Molitor , David C. Molzahn , Stacie Santhany , Abraham D. Schuitman
IPC分类号： C07C209/00 , C07C209/62 , C07C211/12 , C07C211/18
CPC分类号： C07C209/62 , C07C211/12 , C07C211/18 , C07C2601/14
摘要： A process for conversion of aliphatic bicyclic amines to aliphatic diamines including contacting one or more bicyclic amines selected from the group consisting of 3-azabicyclo[3.3.1]nonane and azabicyclo[3.3.1]non-2-ene with ammonia and hydrogen, and alcohols in the presence of heterogeneous metal based catalyst systems, a metal selected from the group consisting of Co, Ni, Ru, Fe, Cu, Re, Pd, and their oxides at a temperature from 140° C. to 200° C. and a pressure from 1540 to 1735 psig for at least one hour reactor systems; forming a product mixture comprising aliphatic diamine(s), bicyclic amine(s), ammonia, hydrogen, and alcohol(s); removing said product mixture from the reactor system; removing at least some of the ammonia, hydrogen, water, alcohols, bicyclic amines from said product mixture; thereby separating the aliphatic diamines from said product mixture.
摘要翻译：包括使一种或多种选自3-氮杂二环[3.3.1]壬烷和氮杂双环[3.3.1]壬-2-烯的二环胺与氨和氢接触，将脂族二环胺转化为脂族二胺的方法，和在非均相金属基催化剂体系存在下的醇，在140℃至200℃的温度下选自Co，Ni，Ru，Fe，Cu，Re，Pd及其氧化物的金属。并且对于至少1小时的反应器系统的压力为1540至1735psig; 形成包含脂族二胺，二环胺，氨，氢和醇的产物混合物; 从反应器系统中除去所述产物混合物; 从所述产物混合物中除去至少一些氨，氢，水，醇，二环胺; 从而从所述产物混合物中分离脂族二胺。

4. 发明授权

US09024072B2 Process for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines 有权
标题翻译：将脂族氰醛还原胺化成脂肪族二胺的方法
公开(公告)号：US09024072B2
公开(公告)日：2015-05-05
申请号：US13383596
申请日：2010-07-30
申请人： Erich J. Molitor , Daniel A. Hickman , Shawn D. Feist , David C. Molzahn , Stacie Santhany , Abraham D. Schuitman
发明人： Erich J. Molitor , Daniel A. Hickman , Shawn D. Feist , David C. Molzahn , Stacie Santhany , Abraham D. Schuitman
IPC分类号： C07C209/00 , C07C209/48
CPC分类号： C07C209/48 , C07C2601/14 , C07C211/18
摘要： A process for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines comprising (1) providing a mixture of 1,3-cyanocyclohexane carboxaldehyde and/or 1,4-cyanocyclohexane carboxaldehyde; (2) contacting said mixture with a metal carbonate based solid bed or a weak base anion exchange resin bed at a temperature from 15 to 40 ° C. for a period of at least 1 minute; (3) thereby treating said mixture, wherein said treated mixture has a pH in the range of 6 to 9; (4) feeding said treated mixture, hydrogen, and ammonia into a continuous reductive amination reactor system; (6) contacting said treated mixture, hydrogen, and ammonia with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature from 80 ° C. to 160 ° C. and a pressure from 700 to 3500 psig; (7) thereby producing one or more cycloaliphatic diamines is provided.
摘要翻译：脂肪族氰醛还原胺化成脂肪族二胺的方法，包括：（1）提供1,3-氰基环己烷甲醛和/或1,4-氰基环己烷甲醛的混合物; （2）将所述混合物与金属碳酸盐基固体床或弱碱性阴离子交换树脂床在15至40℃的温度下接触至少1分钟; （3），从而处理所述混合物，其中所述处理的混合物的pH在6至9的范围内; （4）将所述处理的混合物，氢气和氨进料到连续还原胺化反应器系统中; （6）在一种或多种非均相金属基催化剂体系的存在下，在80℃至160℃的温度和700至3500psig的压力下使所述经处理的混合物，氢气和氨彼此接触; （7），从而产生一种或多种脂环族二胺。

5. 发明申请

US20120136173A1 PROCESS FOR IMPROVING THE CATALYTIC ACTIVITY OF CATALYST SYSTEMS FOR REDUCTIVE AMINATION OF ALIPHATIC CYANOALDEHYDES TO ALIPHATIC DIAMINES 审中-公开
标题翻译：用于改进催化剂系统的催化活性的方法，用于将二烷基氰化物还原成氨基二胺
公开(公告)号：US20120136173A1
公开(公告)日：2012-05-31
申请号：US13383449
申请日：2010-07-30
申请人： Daniel A. Hickman , Shawn D. Feist , Erich J. Molitor , David C. Molzahn , Stacie Santhany , Abraham D. Schuitman
发明人： Daniel A. Hickman , Shawn D. Feist , Erich J. Molitor , David C. Molzahn , Stacie Santhany , Abraham D. Schuitman
IPC分类号： C07C209/00 , C07C211/36 , B01J35/02 , B01J38/66 , B01J38/10
CPC分类号： C07C209/48 , C07C2601/14 , C07C211/18
摘要： The instant invention provides a process for improving catalytic activity of catalyst systems for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines. The process for improving catalytic activity of catalyst systems for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines comprises the steps of: (1) feeding ammonia, optionally hydrogen, and optionally one or more solvents over one or more heterogeneous metal based catalyst systems having a reduced catalytic activity for a period of greater than 1 hour at a temperature in the range of from 50° C. to 500° C.; wherein said one or more heterogeneous metal based catalyst systems have a yield of less than 90 percent based on the molar conversion of cyanoaldehydes to diamines; and (2) thereby improving the catalytic activity of said one or more heterogeneous metal based catalyst systems.
摘要翻译：本发明提供了一种改进用于将脂族氰醛还原胺化成脂族二胺的催化剂体系的催化活性的方法。用于改进用于将脂族氰醛还原胺化成脂肪族二胺的催化剂体系的催化剂体系的方法包括以下步骤：（1）将氨，任选的氢和任选的一种或多种溶剂供给到一种或多种具有减少的催化活性在50℃至500℃的温度下大于1小时; 其中所述一种或多种非均相金属基催化剂体系的产率基于氰醛向二胺的摩尔转化率小于90％; 和（2）从而提高所述一种或多种非均相金属基催化剂体系的催化活性。

6. 发明申请

US20120116123A1 PROCESS FOR SEPARATING ONE OR MORE ALIPHATIC DIAMINES FROM REDUCTIVE AMINATION REACTION SOLVENTS AND IMPURITIES 有权
公开(公告)号：US20120116123A1
公开(公告)日：2012-05-10
申请号：US13383325
申请日：2010-07-30
申请人： Stacie Santhany , Patrick Ho Sing Au-Yeung , Gerald W. Dare , Shawn D. Feist , Barry B. Fish , Daniel A. Hickman , David Jean , Erich J. Molitor , Abraham D. Schuitman , Todd William Toyzan
发明人： Stacie Santhany , Patrick Ho Sing Au-Yeung , Gerald W. Dare , Shawn D. Feist , Barry B. Fish , Daniel A. Hickman , David Jean , Erich J. Molitor , Abraham D. Schuitman , Todd William Toyzan
IPC分类号： C07C209/86 , C07C211/09
CPC分类号： C07C209/86 , C07C2601/14 , C07C211/28
摘要： The instant invention provides a process for separating one or more aliphatic diamines from reductive amination reaction solvents and impurities, and aliphatic diamines obtained via such a process. The process for separating one or more aliphatic diamines from reductive amination reaction solvents and impurities according to the instant invention comprises the steps of: (1) feeding one or more cycloaliphatic cyanoaldehydes, hydrogen, ammonia, and optionally one or more solvents into a continuous reductive amination reactor system; (2) contacting said one or more cycloaliphatic cyanoaldehydes, hydrogen, and ammonia with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature in the range of from 80° C. to about 160° C. and a pressure in the range of from 700 to 3500 psig; (3) thereby forming a product mixture comprising one or more cycloaliphatic diamines, optionally one or more bicyclic by-products, optionally one or more cycloaliphatic aminonitriles, optionally one or more cycloaliphatic aminoalcohols, optionally one or more oligomeric by-products, ammonia, water, hydrogen, and optionally one or more solvents; (4) removing said product mixture from the reactor system; (5) removing at least a portion of said ammonia, said hydrogen, or mixture thereof from said product mixture via distillation; (6) removing at least a portion of said water and said one or more optional solvents via distillation; (7) removing at least a portion of one or more optional bicyclic by-products via distillation; (8) removing one or more optional cycloaliphatic aminonitriles, one or more optional cycloaliphatic aminoalcohols, one or more optional oligomeric by-products via distillation; and (9) thereby separating said one or more cycloaliphatic diamines from said product mixture.

7. 发明授权

US09187403B2 Process for separating one or more aliphatic diamines from reductive amination reaction solvents and impurities 有权
公开(公告)号：US09187403B2
公开(公告)日：2015-11-17
申请号：US13383325
申请日：2010-07-30
申请人： Stacie Santhany , Patrick Ho Sing Au-Yeung , Gerald W. Dare , Shawn D. Feist , Barry B. Fish , Daniel A. Hickman , David Jean , Erich J. Molitor , Abraham D. Schuitman , Todd William Toyzan
发明人： Stacie Santhany , Patrick Ho Sing Au-Yeung , Gerald W. Dare , Shawn D. Feist , Barry B. Fish , Daniel A. Hickman , David Jean , Erich J. Molitor , Abraham D. Schuitman , Todd William Toyzan
IPC分类号： C07C209/00 , C07C209/86
CPC分类号： C07C209/86 , C07C2601/14 , C07C211/28
摘要： The instant invention provides a process for separating one or more aliphatic diamines from reductive amination reaction solvents and impurities, and aliphatic diamines obtained via such a process. The process for separating one or more aliphatic diamines from reductive amination reaction solvents and impurities according to the instant invention comprises the steps of: (1) feeding one or more cycloaliphatic cyanoaldehydes, hydrogen, ammonia, and optionally one or more solvents into a continuous reductive amination reactor system; (2) contacting said one or more cycloaliphatic cyanoaldehydes, hydrogen, and ammonia with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature in the range of from 80° C. to about 160° C. and a pressure in the range of from 700 to 3500 psig; (3) thereby forming a product mixture comprising one or more cycloaliphatic diamines, optionally one or more bicyclic by-products, optionally one or more cycloaliphatic aminonitriles, optionally one or more cycloaliphatic aminoalcohols, optionally one or more oligomeric by-products, ammonia, water, hydrogen, and optionally one or more solvents; (4) removing said product mixture from the reactor system; (5) removing at least a portion of said ammonia, said hydrogen, or mixture thereof from said product mixture via distillation; (6) removing at least a portion of said water and said one or more optional solvents via distillation; (7) removing at least a portion of one or more optional bicyclic by-products via distillation; (8) removing one or more optional cycloaliphatic aminonitriles, one or more optional cycloaliphatic aminoalcohols, one or more optional oligomeric by-products via distillation; and (9) thereby separating said one or more cycloaliphatic diamines from said product mixture.

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