公开(公告)号：US09890096B2

公开(公告)日：2018-02-13

申请号：US13313649

申请日：2011-12-07

申请人： Stephen A. Cottrell ,  Yuon Chiu ,  Haluk Kopkalli ,  Hsueh Sung Tung ,  Kevin D. Uhrich ,  Peter Scheidle

发明人： Stephen A. Cottrell ,  Yuon Chiu ,  Haluk Kopkalli ,  Hsueh Sung Tung ,  Kevin D. Uhrich ,  Peter Scheidle

IPC分类号： C07C17/25 ,  C07C17/38 ,  C07C17/383 ,  C07C17/21 ,  C07C17/20 ,  C07C17/087

CPC分类号： C07C17/21 ,  C07C17/087 ,  C07C17/206 ,  C07C17/25 ,  C07C17/38 ,  C07C17/383 ,  C07C19/10 ,  C07C21/18

摘要： Disclosed is a process for the manufacture of 1234yf from 1,1,2,3-tetrachloropropene, abbreviated herein as “TCP,” in three integrated steps: (a) the R-1 hydrofluorination of TCP to form 1233xf in the vapor phase; (b) the R-2 hydrofluorination of 1233xf to form 244bb in either the liquid phase or in the liquid phase followed by the vapor phase; and (c) the R-3 dehydrochlorination of the 244bb in either the liquid or the vapor phase to produce 1234yf; wherein the vapor phase hydrofluorination of TCP in step (a) is carried out at a higher pressure than the liquid phase hydrofluorination of 1233xf; andwherein the HC1 generated during these steps is scrubbed with water to form an acid solution and the organic components are scrubbed with a caustic solution and then dried before further processing.

公开(公告)号：US20120184785A1

公开(公告)日：2012-07-19

申请号：US13313649

申请日：2011-12-07

申请人： Stephen A. Cottrell ,  Yuon Chiu ,  Haluk Kopkalli ,  Hsueh Sung Tung ,  Kevin D. Uhrich ,  Peter Scheidle

发明人： Stephen A. Cottrell ,  Yuon Chiu ,  Haluk Kopkalli ,  Hsueh Sung Tung ,  Kevin D. Uhrich ,  Peter Scheidle

IPC分类号： C07C21/18

CPC分类号： C07C17/21 ,  C07C17/087 ,  C07C17/206 ,  C07C17/25 ,  C07C17/38 ,  C07C17/383 ,  C07C19/10 ,  C07C21/18

摘要： Disclosed is a process for the manufacture of 1234yf from 1,1,2,3-tetrachloropropene, abbreviated herein as “TCP,” in three integrated steps: (a) the R-1 hydrofluorination of TCP to form 1233xf in the vapor phase; (b) the R-2 hydrofluorination of 1233xf to form 244bb in either the liquid phase or in the liquid phase followed by the vapor phase; and (c) the R-3 dehydrochlorination of the 244bb in either the liquid or the vapor phase to produce 1234yf; wherein the vapor phase hydrofluorination of TCP in step (a) is carried out at a lower pressure than the liquid phase hydrofluorination of 123xf; and wherein the HCl generated during these steps is scrubbed with water to form an acid solution and the organic components are scrubbed with a caustic solution and then dried before further processing.

摘要翻译： 公开了一种在1,1,3,3-四氯丙烯中制备1234yf的方法，在本文中简称为“TCP”，在三个一体化步骤中：（a）TCP的R-1氢氟化在气相中形成1233xf; （b）1233xf的R-2氢氟化在液相或液相中形成244bb，随后是气相; 和（c）244bb在液相或气相中的R-3脱氯化氢以产生1234yf; 其中步骤（a）中TCP的气相氢氟化在比123xf的液相氢氟化更低的压力下进行; 并且其中在这些步骤期间产生的HCl用水洗涤以形成酸溶液，并且用苛性碱溶液洗涤有机组分，然后在进一步加工之前干燥。

公开(公告)号：US20120134892A1

公开(公告)日：2012-05-31

申请号：US13362031

申请日：2012-01-31

申请人： Haluk Kopkalli ,  Yuon Chiu ,  Orlando George Rodrigues ,  Gus Cerri ,  Hsueh Sung Harry Tung ,  Stephen A. Cottrell

发明人： Haluk Kopkalli ,  Yuon Chiu ,  Orlando George Rodrigues ,  Gus Cerri ,  Hsueh Sung Harry Tung ,  Stephen A. Cottrell

IPC分类号： B01J19/00

CPC分类号： B01J8/067 ,  B01J2208/00849 ,  B01J2208/00884 ,  C07C17/354 ,  C07C19/08

摘要： Disclosed is a process and apparatus for the catalytic hydrogenation of fluoro-olefins to fluorocarbons where the reaction is carried out in a multi-tube shell and tube reactor. Reactions involving hydrogenation of fluoro-olefins are typically exothermic. In commercial processes where a fluoro-olefin CnH2n-xFx to CnH2n-x2Fx is hydrogenated (e.g., hexafluoropropylene to 236ea, 1225ye to 245eb, and the like), inadequate management or control of heat removal may induce excess hydrogenation, decomposition and hot spots resulting in reduced yields and potential safety issues. In the hydrogenation of fluoro-olefins, it is therefore necessary to control the reaction temperature as precisely as practical to overcome challenges associated with heat management and safety.

摘要翻译： 公开了将氟代烯烃催化氢化成碳氟化合物的方法和装置，其中反应在多管壳管式反应器中进行。 涉及氟代烯烃氢化的反应通常是放热的。 在氟化烯烃CnH2n-xFx至CnH2n-x2Fx被氢化（例如六氟丙烯至236ea，1225ye至245eb等）的商业过程中，不充分的除热控制或控制可能引起过量氢化，分解和热点，导致 降低产量和潜在的安全问题。 在氟代烯烃的氢化中，因此需要精确地控制反应温度以克服与热管理和安全相关的挑战。

公开(公告)号：US20090287026A1

公开(公告)日：2009-11-19

申请号：US12466271

申请日：2009-05-14

申请人： Haluk Kopkalli ,  Yuon Chiu ,  Hsueh Sung Tung

发明人： Haluk Kopkalli ,  Yuon Chiu ,  Hsueh Sung Tung

IPC分类号： C07C17/25

CPC分类号： C07C21/18 ,  C07C17/087 ,  C07C17/204 ,  C07C17/206 ,  C07C17/25 ,  C07C19/10

摘要： Disclosed is a process for producing tetrafluoropropene comprising: (a) catalytically fluorinating at least one tetrafluoropropene in a first reactor to produce HCFO-1233xf; (b) reacting said HCFO-1233xf with hydrogen fluoride in a second reactor to produce HCFC-244bb; (c) recycling at least a portion of said HCFC-244bb back to said first reactor as recycled HCFC-244bb; and (d) catalytically dehydrochlorinating said recycled HCFC-244bb in said first reactor to produce HFO-1234yf.

摘要翻译： 公开了一种生产四氟丙烯的方法，包括：（a）在第一反应器中催化氟化至少一种四氟丙烯以产生HCFO-1233xf; （b）在第二反应器中使所述HCFO-1233xf与氟化氢反应以产生HCFC-244bb; （c）将所述HCFC-244bb的至少一部分再循环回所述第一反应器作为再循环HCFC-244bb; 和（d）在所述第一反应器中对所述再循环HCFC-244bb进行催化脱氯化氢以产生HFO-1234yf。

公开(公告)号：US6153802A

公开(公告)日：2000-11-28

申请号：US75486

申请日：1998-05-08

申请人： Yuon Chiu

发明人： Yuon Chiu

IPC分类号： A47G25/90 ,  C07B39/00 ,  C07C17/20 ,  C07C17/38 ,  C07C19/08 ,  C07C17/00 ,  B01D3/14

CPC分类号： C07B39/00 ,  C07C17/204 ,  C07C17/206 ,  C07C17/208 ,  C07C17/38 ,  Y02P20/582

摘要： A system and process for producing a fluorinated organic compound, said process comprising (a) reacting an organic compound with a fluorinations agent in the presence of a liquid-phase fluorinations catalyst to produce a product stream; (b) scrubbing said product stream to remove a substantial portion of said catalyst to form a low-catalyst content product stream; and (c) recovering said fluorinated organic compound from said low-catalyst content stream.

摘要翻译： 一种制备含氟有机化合物的体系和方法，所述方法包括（a）在液相氟化催化剂存在下使有机化合物与氟化剂反应以产生产物流; （b）洗涤所述产物流以除去大部分所述催化剂以形成低催化剂含量的产物流; 和（c）从所述低催化剂含量流中回收所述含氟有机化合物。

公开(公告)号：US09255046B2

公开(公告)日：2016-02-09

申请号：US12125045

申请日：2008-05-21

申请人： Stephen A. Cottrell ,  Hsueh Sung Tung ,  Haiyou Wang ,  Yuon Chiu ,  Gustavo Cerri

发明人： Stephen A. Cottrell ,  Hsueh Sung Tung ,  Haiyou Wang ,  Yuon Chiu ,  Gustavo Cerri

IPC分类号： C07C17/00 ,  C07C19/08 ,  C07C21/18 ,  C07C23/00 ,  C07C25/13 ,  C07C17/25 ,  C07C17/358

CPC分类号： C07C17/25 ,  C07C17/358 ,  C07C21/18

摘要： Disclosed is a method for forming HFO-1234ze, and for forming compositions comprising HFO-1234ze, by (a) converting, preferably by dehydrofluorination, pentafluorpropane (HFC-245), preferably 1,1,1,3,3-pentafluorpropane (HFC-245fa), preferably by contact with a caustic solution, to a reaction product comprising cis-HFO-1234ze and trans-HFO-1234ze; and (b) contacting at least a portion, preferably substantially portion, and in certain embodiments substantially all of said reaction product with at least one isomerization catalyst to convert at least a portion, and preferably at least a substantial portion, of cis-HFO-1234ze in said reaction product to trans-HFO-1234ze.

摘要翻译： 公开了形成HFO-1234ze的方法，以及用于形成包含HFO-1234ze的组合物的方法，通过（a）优选通过脱氟化氢转化五氟丙烷（HFC-245），优选1,1,1,3,3-五氟丙烷（HFC -245fa），优选通过与苛性碱溶液接触，加入到包含顺-HFO-1234ze和反-HFO-1234ze的反应产物中; 并且（b）使至少一部分，优选基本上部分，在某些实施方案中使基本上所有的所述反应产物与至少一种异构化催化剂接触，以将至少一部分，优选至少大部分的顺-HFO- 1234ze在所述反应产物中以反式HFO-1234ze。

公开(公告)号：US08969634B2

公开(公告)日：2015-03-03

申请号：US13245328

申请日：2011-09-26

申请人： Yuon Chiu ,  Haluk Kopkalli ,  Richard Durick Horwath

发明人： Yuon Chiu ,  Haluk Kopkalli ,  Richard Durick Horwath

IPC分类号： C07C17/00 ,  C07C21/00 ,  C07C17/354 ,  B01J8/04 ,  B01J8/06

CPC分类号： B01J8/067 ,  B01J8/0207 ,  B01J8/048 ,  B01J8/0492 ,  B01J8/0496 ,  B01J8/065 ,  B01J2208/00221 ,  B01J2208/00902 ,  B01J2208/00929 ,  B01J2208/02 ,  B01J2208/065 ,  C07C17/354 ,  Y02P20/124 ,  C07C19/08

摘要： The present invention is directed to a combination reactor system for exothermic reactions comprising a trickle-bed reactor and a shell-and-tube reactor. This combination allows the system to efficiently remove heat while also providing the ability to control both the temperature and/or reaction progression. The trickle-bed reactor removes heat efficiently from the system by utilizing latent heat and does not require the use of a cooling or heating medium. The shell-and-tube reactor is used to further progress the reaction and provides a heat exchanger in order to introduce fluid at the desired temperature in the shell-and-tube reactor. Also, additional reactant or reactants and/or other fluids may be introduced to the shell-and-tube section of the reactor under controlled temperature conditions.

摘要翻译： 本发明涉及一种用于放热反应的组合反应器系统，其包括滴流床反应器和管壳式反应器。 该组合允许系统有效地除去热量，同时还提供控制温度和/或反应进程的能力。 滴流反应器通过利用潜热从系统中有效地除去热量，并且不需要使用冷却或加热介质。 使用壳管式反应器进一步进行反应并提供热交换器以便在壳管式反应器中将所需温度的流体引入。 此外，可以在受控的温度条件下将另外的反应物或反应物和/或其它流体引入反应器的管壳部分。

公开(公告)号：US20130079563A1

公开(公告)日：2013-03-28

申请号：US13245328

申请日：2011-09-26

申请人： Yuon Chiu ,  Haluk Kopkalli ,  Richard Durick Horwath

发明人： Yuon Chiu ,  Haluk Kopkalli ,  Richard Durick Horwath

IPC分类号： C07C19/08 ,  B01J8/04

CPC分类号： B01J8/067 ,  B01J8/0207 ,  B01J8/048 ,  B01J8/0492 ,  B01J8/0496 ,  B01J8/065 ,  B01J2208/00221 ,  B01J2208/00902 ,  B01J2208/00929 ,  B01J2208/02 ,  B01J2208/065 ,  C07C17/354 ,  Y02P20/124 ,  C07C19/08

摘要： The present invention is directed to a combination reactor system for exothermic reactions comprising a trickle-bed reactor and a shell-and-tube reactor. This combination allows the system to efficiently remove heat while also providing the ability to control both the temperature and/or reaction progression. The trickle-bed reactor removes heat efficiently from the system by utilizing latent heat and does not require the use of a cooling or heating medium. The shell-and-tube reactor is used to further progress the reaction and provides a heat exchanger in order to introduce fluid at the desired temperature in the shell-and-tube reactor. Also, additional reactant or reactants and/or other fluids may be introduced to the shell-and-tube section of the reactor under controlled temperature conditions.

公开(公告)号：US20110207974A9

公开(公告)日：2011-08-25

申请号：US12466271

申请日：2009-05-14

申请人： Haluk Kopkalli ,  Yuon Chiu ,  Hsueh Sung Tung

发明人： Haluk Kopkalli ,  Yuon Chiu ,  Hsueh Sung Tung

IPC分类号： C07C17/25

CPC分类号： C07C21/18 ,  C07C17/087 ,  C07C17/204 ,  C07C17/206 ,  C07C17/25 ,  C07C19/10

摘要： Disclosed is a process for producing tetrafluoropropene comprising: (a) catalytically fluorinating at least one tetrafluoropropene in a first reactor to produce HCFO-1233xf; (b) reacting said HCFO-1233xf with hydrogen fluoride in a second reactor to produce HCFC-244bb; (c) recycling at least a portion of said HCFC-244bb back to said first reactor as recycled HCFC-244bb; and (d) catalytically dehydrochlorinating said recycled HCFC-244bb in said first reactor to produce HFO-1234yf.

摘要翻译： 公开了一种生产四氟丙烯的方法，包括：（a）在第一反应器中催化氟化至少一种四氟丙烯以产生HCFO-1233xf; （b）在第二反应器中使所述HCFO-1233xf与氟化氢反应以产生HCFC-244bb; （c）将所述HCFC-244bb的至少一部分再循环回所述第一反应器作为再循环HCFC-244bb; 和（d）在所述第一反应器中对所述再循环HCFC-244bb进行催化脱氯化氢以产生HFO-1234yf。

公开(公告)号：US20100307726A1

公开(公告)日：2010-12-09

申请号：US12481107

申请日：2009-06-09

申请人： Yuon Chiu ,  Stephen A. Cottrell ,  Richard Durick Horwath ,  Haluk Kopkalli

发明人： Yuon Chiu ,  Stephen A. Cottrell ,  Richard Durick Horwath ,  Haluk Kopkalli

IPC分类号： F28F9/02

CPC分类号： F28D7/1638 ,  B01J8/067 ,  B01J2208/00221 ,  B01J2208/0023 ,  F28F9/0202 ,  F28F9/0265 ,  F28F2009/226 ,  F28F2210/08

摘要： A multi-stage, multi-tube, shell-and-tube reactor which contains reaction zones and interstage temperature control (cooling/heating) zones in series. The reactor has at least two types of zones which both contribute to removing or supplying heat to the system depending on the system's need. The reactor will have a group of reaction zones which contain tubes packed with catalyst to progress the reaction and remove or supply heat simultaneously. There are also a number of interstage temperature control (cooling/heating) zones which are designed to supply or remove heat to or from the system. The positioning, number, and design of the zones will depend on the amount of temperature control desired and exothermic or endothermic nature of the processes to be conducted in the reactor.

摘要翻译： 包含反应区和级间温度控制（冷却/加热）区的多级，多管，管壳式反应器。 反应器具有至少两种类型的区域，这两个区域有助于根据系统的需要去除或供应热量。 反应器将具有一组反应区，其中包含装有催化剂的管，以进行反应并同时除去或提供热量。 还有一些级间温度控制（冷却/加热）区域，其设计用于向系统或从系统提供或移除热量。 区域的定位，数量和设计将取决于在反应器中进行的方法所需的温度控制量和放热或吸热性质。