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1. 发明授权

US08080677B2 Process for selective oxidation of olefins to epoxides 有权
标题翻译：将烯烃选择性氧化成环氧化物的方法
公开(公告)号：US08080677B2
公开(公告)日：2011-12-20
申请号：US12206335
申请日：2008-09-08
申请人： Bala Subramaniam , Daryle H. Busch , Hyun-Jin Lee , Madhav Ghanta , Tie-Pan Shi
发明人： Bala Subramaniam , Daryle H. Busch , Hyun-Jin Lee , Madhav Ghanta , Tie-Pan Shi
IPC分类号： C07D303/00
CPC分类号： C07D301/12 , Y02P20/582
摘要： A process for the selective oxidation of olefins to epoxides comprising the step of contacting the olefin (propylene or ethylene) with an oxidant (hydrogen peroxide) in the presence of a Lewis acid oxidation catalyst (MTO), organic base (pyridine or its N-oxide), in a solvent system comprising an organic water-miscible solvent (methanol). The system is pressurized using either the olefin itself or by adding an inert pressurizing gas (nitrogen) to increase the pressure between 230 and 700 psi at a temperature between 0.7 and 1.3 times the critical temperature of the olefin. The resulting increased solubility of the olefin in the organic solvent system increases the selectivity and yield of the desired epoxide (propylene oxide or ethylene oxide).
摘要翻译：一种将烯烃选择性氧化成环氧化物的方法，包括在路易斯酸氧化催化剂（MTO），有机碱（吡啶或其N-氧化物）存在下使烯烃（丙烯或乙烯）与氧化剂（过氧化氢）接触的步骤，氧化物），在包含有机水混溶性溶剂（甲醇）的溶剂体系中。使用烯烃本身或通过加入惰性加压气体（氮气）来加压系统，以在烯烃的临界温度的0.7至1.3倍之间的温度下增加230至700psi之间的压力。所产生的烯烃在有机溶剂体系中的溶解度增加了所需环氧化物（环氧丙烷或环氧乙烷）的选择性和产率。

2. 发明授权

US07649101B2 Process for selective oxidation of olefins to epoxides 有权
标题翻译：将烯烃选择性氧化成环氧化物的方法
公开(公告)号：US07649101B2
公开(公告)日：2010-01-19
申请号：US11586061
申请日：2006-10-25
申请人： Daryle H. Busch , Bala Subramaniam , Hyun-Jin Lee , Tie-Pan Shi
发明人： Daryle H. Busch , Bala Subramaniam , Hyun-Jin Lee , Tie-Pan Shi
IPC分类号： C07D301/12
CPC分类号： C07D301/12 , Y02P20/582
摘要： A process for the selective oxidation of olefins to epoxides comprising the step of contacting the olefin (propylene) with an oxidant (hydrogen peroxide) in the presence of a Lewis acid oxidation catalyst (MTO), organic base (pyridine or its N-oxide), in a solvent system comprising an organic water-miscible solvent (methanol); and adding a pressurizing gas (nitrogen) to increase the pressure, whereby olefin is further dissolved in organic solvent system to increase the selectivity and yield of the desired epoxide (propylene oxide).
摘要翻译：一种将烯烃选择性氧化成环氧化物的方法，包括在路易斯酸氧化催化剂（MTO），有机碱（吡啶或其N-氧化物）存在下使烯烃（丙烯）与氧化剂（过氧化氢）接触的步骤，，在包含有机水混溶性溶剂（甲醇）的溶剂体系中; 并加入加压气体（氮气）以增加压力，从而使烯烃进一步溶解在有机溶剂体系中以提高所需环氧化物（环氧丙烷）的选择性和产率。

3. 发明申请

US20090131693A1 Process for Selective Oxidation of Olefins to Epoxides 有权
标题翻译：烯烃选择性氧化成环氧化物的方法
公开(公告)号：US20090131693A1
公开(公告)日：2009-05-21
申请号：US12206335
申请日：2008-09-08
申请人： Daryle H. Busch , Bala Subramaniam , Hyun-Jin Lee , Tie-Pan Shi
发明人： Daryle H. Busch , Bala Subramaniam , Hyun-Jin Lee , Tie-Pan Shi
IPC分类号： C07D301/03 , C07D301/12 , C09K3/00
CPC分类号： C07D301/12 , Y02P20/582
摘要： A process for the selective oxidation of olefins to epoxides comprising the step of contacting the olefin (propylene or ethylene) with an oxidant (hydrogen peroxide) in the presence of a Lewis acid oxidation catalyst (MTO), organic base (pyridine or its N-oxide), in a solvent system comprising an organic water-miscible solvent (methanol). The system is pressurized using either the olefin itself or by adding an inert pressurizing gas (nitrogen) to increase the pressure between 230 and 700 psi at a temperature between 0.7 and 1.3 times the critical temperature of the olefin. The resulting increased solubility of the olefin in the organic solvent system increases the selectivity and yield of the desired epoxide (propylene oxide or ethylene oxide).
摘要翻译：一种将烯烃选择性氧化成环氧化物的方法，包括在路易斯酸氧化催化剂（MTO），有机碱（吡啶或其N-氧化物）存在下使烯烃（丙烯或乙烯）与氧化剂（过氧化氢）接触的步骤，氧化物），在包含有机水混溶性溶剂（甲醇）的溶剂体系中。使用烯烃本身或通过加入惰性加压气体（氮气）来加压系统，以在烯烃的临界温度的0.7至1.3倍之间的温度下增加230至700psi之间的压力。所产生的烯烃在有机溶剂体系中的溶解度增加了所需环氧化物（环氧丙烷或环氧乙烷）的选择性和产率。

4. 发明授权

US06740785B2 Catalytic oxidation of organic substrates by transition metal complexes in organic solvent media expanded by supercritical or subcritical carbon dioxide 有权
标题翻译：通过过渡金属配合物在有机溶剂介质中通过超临界或亚临界二氧化碳膨胀来催化氧化有机底物
公开(公告)号：US06740785B2
公开(公告)日：2004-05-25
申请号：US10205863
申请日：2002-07-26
申请人： Bala Subramaniam , Daryle H. Busch , Ghezai T. Musie , Ming Wei
发明人： Bala Subramaniam , Daryle H. Busch , Ghezai T. Musie , Ming Wei
IPC分类号： C07C3700
CPC分类号： C07D303/04 , C07B41/00 , C07C27/12 , C07C29/50 , C07C45/34 , C07C46/08 , C07C2601/14 , C07C2601/16 , C07D301/06 , Y02P20/544 , C07C49/713 , C07C49/603 , C07C35/14 , C07C35/18
摘要： Improved oxidation methods are provided wherein a reaction mixture comprising a substrate to be oxidized (e.g., phenols, alkenes) and an oxidation catalyst (typically dispersed in an organic solvent system) is supplemented with a compressed gas which expands the reaction mixture, thus accelerating the oxidation reaction. In preferred practice pressurized subcritical or supercritical carbon dioxide is used as the expanding gas, which is introduced into the reaction mixture together with an oxidizing agent. The inventive methods improve the substrate conversion and product selectivity by increasing the solubility of the oxidizing agent in the reaction mixture.
摘要翻译：提供了改进的氧化方法，其中包含待氧化的基质（例如酚，烯烃）和氧化催化剂（通常分散在有机溶剂体系中）的反应混合物补充有膨胀反应混合物的压缩气体，从而加速氧化反应。在优选的实践中，使用加压亚临界或超临界二氧化碳作为膨胀气体，其与氧化剂一起引入反应混合物。本发明的方法通过增加氧化剂在反应混合物中的溶解度来改善底物转化率和产物选择性。

5. 发明授权

US09238608B2 Spray process for selective oxidation 有权
标题翻译：用于选择性氧化的喷涂工艺
公开(公告)号：US09238608B2
公开(公告)日：2016-01-19
申请号：US13258159
申请日：2010-03-23
申请人： Bala Subramaniam , Daryle H. Busch , Fenghul Niu
发明人： Bala Subramaniam , Daryle H. Busch , Fenghul Niu
IPC分类号： C07C51/265 , C07C51/255 , B01J4/00 , B01J10/00
CPC分类号： C07C51/255 , B01J4/002 , B01J10/007 , B01J2219/00006 , B01J2219/00063 , B01J2219/00065 , B01J2219/00162 , C07C51/265 , C07C63/00
摘要： Oxidation process can include: introducing small droplets of liquid reaction mixture having oxidizable reactant, catalyst, and solvent into a reaction zone containing oxygen and diluent gas; and oxidizing the reactant with the oxygen at a suitable reaction temperature and a suitable reaction pressure to produce an oxidized product. The liquid reaction mixture can have an aromatic feedstock having an oxidizable substituent as the oxidizable reactant. The oxidized product can include an aromatic compound having at least one carboxylic acid. For example, the aromatic feedstock can include a benzene ring having at least one oxidizable alkyl substituent, furan hetero-ring having at least one oxidizable alkyl substituent, a naphthalene poly-ring having at least one oxidizable alkyl substituent, derivatives thereof, and mixtures thereof.
摘要翻译：氧化过程可以包括：将具有可氧化反应物，催化剂和溶剂的小液滴的液体反应混合物引入含有氧气和稀释气体的反应区; 并在合适的反应温度和合适的反应压力下用氧氧化反应物以产生氧化产物。液体反应混合物可具有具有可氧化取代基的芳族原料作为可氧化反应物。氧化产物可以包括具有至少一个羧酸的芳族化合物。例如，芳族原料可以包括具有至少一个可氧化烷基取代基的苯环，具有至少一个可氧化烷基取代基的呋喃异环，具有至少一个可氧化烷基取代基的萘多环，其衍生物及其混合物。

6. 发明申请

US20140343305A1 PROCESS FOR PRODUCING BOTH BIOBASED SUCCINIC ACID AND 2,5-FURANDICARBOXYLIC ACID 审中-公开
标题翻译：生产双酚化酸和2,5-呋喃糖基酸的方法
公开(公告)号：US20140343305A1
公开(公告)日：2014-11-20
申请号：US14239822
申请日：2012-08-28
申请人： Bala Subramaniam , Xiaobin Zuo , Daryle H. Busch , Padmesh Venkitasubramaniam
发明人： Bala Subramaniam , Xiaobin Zuo , Daryle H. Busch , Padmesh Venkitasubramaniam
IPC分类号： C07D307/68 , C07C51/245
CPC分类号： C07D307/68 , C07C51/245 , C07D307/46 , C07C55/10
摘要： A process is provided for carrying out an oxidation on a feed including levulinic acid and/or a levulinic acid oxidation precursor to succinic acid, one or more furanic oxidation precursors of 2,5-furandicarboxylic acid and a catalytically effective combination of cobalt, manganese, and bromide components for catalyzing the oxidation of the levulinic acid component and of the one or more furanic oxidation precursors to produce both succinic acid and 2,5-furandicarboxylic acid products, which process comprises supplying the feed to a reactor vessel, supplying an oxidant, reacting the levulinic acid component and the one or more furanic oxidation precursors with the oxidant to produce both succinic acid and 2,5-furandicarboxylic acid (FDCA) and then recovering the succinic acid and FDCA products. A crude dehydration product from the dehydration of fructose, glucose or both, including 5-hydroxymethylfurfural, can be directly oxidized by the process to produce 2,5-furandicarboxylic acid and succinic acid.
摘要翻译：提供了一种方法，用于在包含乙酰丙酸和/或乙酰丙酸氧化前体的进料上进行氧化，所述前体包含琥珀酸，一种或多种2,5-呋喃二羧酸的呋喃氧化前体和催化有效的钴，锰，以及用于催化乙酰丙酸组分和一种或多种呋喃氧化前体的氧化以产生琥珀酸和2,5-呋喃二羧酸产物的溴化物组分，该方法包括将进料供应到反应器容器中，供应氧化剂，使乙酰丙酸组分和一种或多种呋喃氧化前体与氧化剂反应以产生琥珀酸和2,5-呋喃二羧酸（FDCA），然后回收琥珀酸和FDCA产物。由脱水果糖，葡萄糖或两者（包括5-羟甲基糠醛）的粗脱水产物可直接氧化，生成2,5-呋喃二羧酸和琥珀酸。

7. 发明授权

US09586923B2 Spray oxidation process for producing 2,5-furandicarboxylic acid from hydroxymethylfurfural 有权
标题翻译：用于从羟甲基糠醛制备2,5-呋喃二羧酸的喷雾氧化法
公开(公告)号：US09586923B2
公开(公告)日：2017-03-07
申请号：US14239819
申请日：2012-08-28
申请人： Bala Subramaniam , Xiaobin Zuo , Daryle H. Busch , Padmesh Venkitasubramanian
发明人： Bala Subramaniam , Xiaobin Zuo , Daryle H. Busch , Padmesh Venkitasubramanian
IPC分类号： C07D307/68 , B01J2/02 , B01J27/128 , B01J19/10 , B01J19/24 , B01J4/00 , C07D307/46 , B01J31/04
CPC分类号： C07D307/68 , B01J2/02 , B01J4/002 , B01J19/10 , B01J19/24 , B01J27/128 , B01J31/04 , B01J2219/00006 , B01J2219/00058 , B01J2219/00065 , B01J2219/00083 , B01J2219/00159 , B01J2219/00164 , B01J2231/763 , C07D307/46
摘要： A process is provided for carrying out an oxidation on a sprayable feed including a furanic substrate to be oxidized and a catalytically effective combination of cobalt, manganese, and bromide components for catalyzing the oxidation of the furanic substrate, which process comprises spraying the feed into a reactor vessel as a mist, supplying an oxidant, reacting the furanic substrate and the oxidant, and managing the exothermic temperature rise due to the reaction through a selection and control of the operating pressure within the reactor vessel. A crude dehydration product from the dehydration of fructose, glucose or both, including 5-hydroxymethylfurfural, can be directly oxidized by the process to produce 2,5-furandicarboxylic acid in surprisingly increased yields.
摘要翻译：提供了一种用于在可喷射进料上进行氧化的方法，所述可喷涂进料包括待氧化的呋喃底物和用于催化呋喃基底氧化的钴，锰和溴组分的催化有效组合，该方法包括将进料喷入反应容器作为雾，供应氧化剂，使呋喃基质和氧化剂反应，并且通过选择和控制反应器容器内的操作压力来控制由反应引起的放热温度升高。果糖，葡萄糖或两者的脱水（包括5-羟甲基糠醛）的粗脱水产物可以通过该方法直接氧化，从而以令人惊讶的增加的产量产生2,5-呋喃二羧酸。

8. 发明申请

US20150183755A1 SPRAY OXIDATION PROCESS FOR PRODUCING 2,5-FURANDICARBOXYLIC ACID FROM HYDROXYMETHYLFURFURAL 审中-公开
标题翻译：用于从羟基甲基纤维生产2,5-呋喃甲酸的喷雾氧化方法
公开(公告)号：US20150183755A1
公开(公告)日：2015-07-02
申请号：US14239819
申请日：2012-08-28
申请人： Bala Subramaniam , Xiaobin Zuo , Daryle H. Busch , Padmesh Venkitasubramanian
发明人： Bala Subramaniam , Xiaobin Zuo , Daryle H. Busch , Padmesh Venkitasubramanian
IPC分类号： C07D307/68
CPC分类号： C07D307/68 , B01J2/02 , B01J4/002 , B01J19/10 , B01J19/24 , B01J27/128 , B01J31/04 , B01J2219/00006 , B01J2219/00058 , B01J2219/00065 , B01J2219/00083 , B01J2219/00159 , B01J2219/00164 , B01J2231/763 , C07D307/46
摘要： A process is provided for carrying out an oxidation on a sprayable feed including a furanic substrate to be oxidized and a catalytically effective combination of cobalt, manganese, and bromide components for catalyzing the oxidation of the furanic substrate, which process comprises spraying the feed into a reactor vessel as a mist, supplying an oxidant, reacting the furanic substrate and the oxidant, and managing the exothermic temperature rise due to the reaction through a selection and control of the operating pressure within the reactor vessel. A crude dehydration product from the dehydration of fructose, glucose or both, including 5-hydroxymethylfurfural, can be directly oxidized by the process to produce 2,5-furandicarboxylic acid in surprisingly increased yields.
摘要翻译：提供了一种用于在可喷射进料上进行氧化的方法，所述可喷涂进料包括待氧化的呋喃底物和用于催化呋喃基底氧化的钴，锰和溴组分的催化有效组合，该方法包括将进料喷入反应容器作为雾，供应氧化剂，使呋喃基质和氧化剂反应，并且通过选择和控制反应器容器内的操作压力来控制由反应引起的放热温度升高。果糖，葡萄糖或两者的脱水（包括5-羟甲基糠醛）的粗脱水产物可以通过该方法直接氧化，从而以令人惊讶的增加的产量产生2,5-呋喃二羧酸。

9. 发明申请

US20120022287A1 Spray Process for Selective Oxidation 有权
标题翻译：选择氧化喷涂工艺
公开(公告)号：US20120022287A1
公开(公告)日：2012-01-26
申请号：US13258159
申请日：2010-03-23
申请人： Bala Subramaniam , Daryle H. Busch , Fenghul Niu
发明人： Bala Subramaniam , Daryle H. Busch , Fenghul Niu
IPC分类号： C07C51/265
CPC分类号： C07C51/255 , B01J4/002 , B01J10/007 , B01J2219/00006 , B01J2219/00063 , B01J2219/00065 , B01J2219/00162 , C07C51/265 , C07C63/00
摘要： Oxidation process can include: introducing small droplets of liquid reaction mixture having oxidizable reactant, catalyst, and solvent into a reaction zone containing oxygen and diluent gas; and oxidizing the reactant with the oxygen at a suitable reaction temperature and a suitable reaction pressure to produce an oxidized product. The liquid reaction mixture can have an aromatic feedstock having an oxidizable substituent as the oxidizable reactant. The oxidized product can include an aromatic compound having at least one carboxylic acid. For example, the aromatic feedstock can include a benzene ring having at least one oxidizable alkyl substituent, furan hetero-ring having at least one oxidizable alkyl substituent, a naphthalene poly-ring having at least one oxidizable alkyl substituent, derivatives thereof, and mixtures thereof.
摘要翻译：氧化过程可以包括：将具有可氧化反应物，催化剂和溶剂的小液滴的液体反应混合物引入含有氧气和稀释气体的反应区; 并在合适的反应温度和合适的反应压力下用氧氧化反应物以产生氧化产物。液体反应混合物可具有具有可氧化取代基的芳族原料作为可氧化反应物。氧化产物可以包括具有至少一个羧酸的芳族化合物。例如，芳族原料可以包括具有至少一个可氧化烷基取代基的苯环，具有至少一个可氧化烷基取代基的呋喃异环，具有至少一个可氧化烷基取代基的萘多环，其衍生物及其混合物。

10. 发明申请

US20080139841A1 Cobalt-Catalyzed Oxidations in Volumetrically Expanded Liquids by Compressed Gases 有权
标题翻译：通过压缩气体在体积膨胀液体中的钴催化氧化
公开(公告)号：US20080139841A1
公开(公告)日：2008-06-12
申请号：US11934612
申请日：2007-11-02
申请人： Richard S. Givens , Chi Cheng Ma , Daryle H. Busch , Bala Subramaniam , Bhuma Rajagopalan
发明人： Richard S. Givens , Chi Cheng Ma , Daryle H. Busch , Bala Subramaniam , Bhuma Rajagopalan
IPC分类号： C07C51/21 , C07C27/12 , C07C45/00 , C07C33/18
CPC分类号： C07C45/33 , C07C45/34 , C07C45/35 , C07C45/36 , C07C51/235 , C07C51/265 , C07C51/313 , C07C67/05 , C07C205/57 , C07C2601/14 , C07C49/12 , C07C49/403 , C07C49/603 , C07C49/597 , C07C47/22 , C07C49/78 , C07C63/26 , C07C63/16 , C07C63/24 , C07C59/84 , C07C55/02 , C07C55/14 , C07C59/347 , C07C69/013 , C07C69/003 , C07C69/16 , C07C69/145
摘要： Oxidations of hydrocarbons, cycloalkanes and alkenes, arylalkanes, and a variety of other organic substrates are accomplished by cobalt-N-hydroxysuccinimide co-catalyzed reactions with dioxygen under unusually mild, near ambient conditions of temperature and pressure. The improved safety of the oxidation method and the high yields of product obtained make use of a unique combination of cobalt (II) complexes with N-hydroxysuccinimide. These autoxidation reactions do not have prolonged initiation times. Many of these reactions can be safely performed under normal chemical laboratory conditions and do not require specialized equipment or reagents.
摘要翻译：碳氢化合物，环烷烃和烯烃，芳基烷烃和各种其他有机基质的氧化通过钴 - N-羟基琥珀酰亚胺与二氧化碳的共催化反应在异常温和的近环境温度和压力条件下完成。获得的产物的氧化方法的改进的安全性和高产率使得钴（II）配合物与N-羟基琥珀酰亚胺的独特组合。这些自氧化反应没有延长的引发时间。许多这些反应可以在正常的化学实验室条件下安全地进行，并且不需要专门的设备或试剂。

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