公开(公告)号：US20100187088A1

公开(公告)日：2010-07-29

申请号：US12749207

申请日：2010-03-29

Applicant: Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh S. Tung ,  Hang T. Pham ,  Rajiv R. Singh

Inventor： Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh S. Tung ,  Hang T. Pham ,  Rajiv R. Singh

IPC: B01D3/36

CPC classification number: B01D3/36 ,  C07C17/386 ,  C07C19/10 ,  C07C21/18

Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf) by adding a third component and then separating via conventional distillation. More particularly the invention pertains to a method for separating HCFC-244bb from HCFC-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).

Abstract translation: 本发明提供一种分离卤代烃的方法。 特别是通过添加第三成分分离2-氯-3,3,3-三氟丙烯（HCFC-1233xf）而分离出2-氯-1,1,1,2-四氟丙烷（HCFC-244bb）的方法， 通过常规蒸馏。 更具体地说，本发明涉及从HCFC-1233xf中分离HCFC-244bb的方法，其可用作制备2,3,3,3-四氟丙烯（HFO-1234yf）中的中间体。

公开(公告)号：US20100048961A1

公开(公告)日：2010-02-25

申请号：US12540252

申请日：2009-08-12

Applicant: Daniel C. Merkel ,  Hsueh Sung Tung ,  Konstantin A. Pokrovski

Inventor： Daniel C. Merkel ,  Hsueh Sung Tung ,  Konstantin A. Pokrovski

IPC: C07C17/20 ,  C07C17/38

CPC classification number: C07C17/392 ,  C07C17/087 ,  C07C17/25 ,  C07C17/38 ,  C07C21/18 ,  C07C19/10

Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) based on differences in melting points of these compounds. More particularly the invention pertains to a method for separating HCFC-244bb from HCFO-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).

Abstract translation: 本发明提供一种分离卤代烃的方法。 特别地，基于这些的熔点的差异，从2-氯-3,3,3-三氟丙烯（HCFO-1233xf）中分离出2-氯-1,1,1,2-四氟丙烷（HCFC-244bb）的方法 化合物。 更具体地说，本发明涉及从HCFO-1233xf中分离HCFC-244bb的方法，其可用作生产2,3,3,3-四氟丙烯（HFO-1234yf）中的中间体。

公开(公告)号：US09938212B2

公开(公告)日：2018-04-10

申请号：US13432300

申请日：2012-03-28

Applicant: Konstantin A. Pokrovski ,  Daniel C. Merkel ,  Haiyou Wang ,  Hsueh Sung Tung

Inventor： Konstantin A. Pokrovski ,  Daniel C. Merkel ,  Haiyou Wang ,  Hsueh Sung Tung

IPC: C07C17/25 ,  C07C17/20 ,  C07C17/38 ,  C07C17/383 ,  C07C17/395 ,  C07C17/21

CPC classification number: C07C17/25 ,  C07C17/206 ,  C07C17/208 ,  C07C17/21 ,  C07C17/38 ,  C07C17/383 ,  C07C17/395 ,  Y02P20/125 ,  Y02P20/582 ,  C07C21/18 ,  C07C19/08

Abstract: Disclosed is an integrated manufacturing process to co-produce (E) 1-chloro-3,3,3-trifluoropropene, (E) 1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoro-propane starting from a single starting feed material or a mixture of unsaturated hydrochlorocarbon feed materials comprising 1,1,1,3-tetrachloropropene and/or 1,1,3,3-tetrachloropropene. The process includes a combined liquid or vapor phase reaction/purification operation which directly produces (E) 1-chloro-3,3,3-trifluoro-propene (1233zd (E)) from these feed materials, which may also include 240fa. In the second liquid phase fluorination reactor 1233zd (E) is contacted with HF in the presence of catalyst to produce 1,1,1,3,3-pentafluoropropane (245fa) with high conversion and selectivity. A third reactor is used for dehydrofluorination of 245fa to produce (E) 1,3,3,3-tetrafluoropropene (1234ze (E)) by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrofluorination catalyst. This operation may be followed by one or more purification processes to recover the 1234ze (E) product.

公开(公告)号：US09000240B2

公开(公告)日：2015-04-07

申请号：US13471565

申请日：2012-05-15

Applicant: Stephen A. Cottrell ,  Hsueh Sung Tung ,  Konstantin A. Pokrovski

Inventor： Stephen A. Cottrell ,  Hsueh Sung Tung ,  Konstantin A. Pokrovski

IPC: C07C17/25 ,  C07C17/20 ,  C07C21/18 ,  C07C17/38 ,  C07C17/383

CPC classification number: C07C17/383 ,  C07C17/206 ,  C07C17/25 ,  C07C17/38 ,  C07C21/18 ,  Y02P20/125

Abstract: The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.

Abstract translation: 本发明涉及以商业规模从240fa和HF生产1233zd（有或没有催化剂）的方法。 将240fa和HF进料到在高压下操作的反应器。 将包含1233zd，HCl，HF和其他副产物的所得产物流处理成一种或多种纯化技术，包括相分离和一种或多种蒸馏以提供满足商业产品规格的纯化的1233zd，即GC纯度为99.5％ 或更大。

公开(公告)号：US08796493B2

公开(公告)日：2014-08-05

申请号：US13249342

申请日：2011-09-30

Applicant: Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung

Inventor： Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung

IPC: C07C17/38

CPC classification number: C07C17/389 ,  B01D15/00 ,  C07C21/18

Abstract: The present invention provides a method for separating halocarbons. In particular, the invention provides a method for separating halogenated olefin impurities from 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) using a solid adsorbent, particularly activated carbon. More particularly the invention pertains to a method for separating 2-chloro-3,3,3-trifluoro-propene (HCFO-1233xf) from HCFC-244bb, which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).

Abstract translation: 本发明提供一种分离卤代烃的方法。 特别地，本发明提供了使用固体吸附剂，特别是活性炭从2-氯-1,1,1,2-四氟丙烷（HCFC-244bb）分离卤代烯烃杂质的方法。 更具体地说，本发明涉及从HCFC-244bb中分离出2-氯-3,3,3-三氟丙烯（HCFO-1233xf）的方法，它们可用作制备2,3,3,3-三氟丙烯 四氟丙烯（HFO-1234yf）。

公开(公告)号：US08704017B2

公开(公告)日：2014-04-22

申请号：US13220212

申请日：2011-08-29

Applicant: Konstantin A. Pokrovski ,  Daniel C. Merkel ,  Hsueh Sung Tung

Inventor： Konstantin A. Pokrovski ,  Daniel C. Merkel ,  Hsueh Sung Tung

IPC: C07C17/20

CPC classification number: C07C17/20 ,  B01D3/009 ,  C01B7/0706 ,  C01B7/0712 ,  C07C17/206 ,  C07C17/25 ,  C07C17/358 ,  C07C17/383 ,  C07C21/18 ,  Y02P20/582

Abstract: Disclosed is process for the production of (E) 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)) by conducting a continuous reaction without the use of a catalyst. Also disclosed is an integrated system for producing hydrofluoro olefins, particularly 1233zd(E). The manufacturing process includes six major unit operations: (1) a fluorination reaction of HCC-240fa (in continuous or semi-batch mode) using HF with simultaneous removal of by-product HCl and the product 1233zd(E); (2) recycle of unreacted HCC-240fa and HF together with under-fluorinated by-products back to (1); (3) separation and purification of by-product HCl; (4) separation of excess HF back to (1); (5) purification of final product, 1233zd(E); and (6) isomerization of by-product 1233zd(Z) to 1233zd(E) to maximize the process yield.

Abstract translation: 公开了通过在不使用催化剂的情况下进行连续反应来制备（E）1-氯-3,3,3-三氟丙烯（HCFO-1233zd（E））的方法。 还公开了用于制备氢氟烯烃的综合系统，特别是1233zd（E）。 制造过程包括六个主要单元操作：（1）使用HF同时除去副产物HCl和产物1233zd（E）的HCC-240fa（连续或半间歇模式）的氟化反应; （2）将未反应的HCC-240fa和HF与未氟化的副产物一起回收至（1）; （3）副产物HCl的分离纯化; （4）将过量的HF分离回（1）; （5）最终产物的纯化，1233zd（E）; 和（6）副产物1233zd（Z）异构化为1233zd（E）以使工艺产率最大化。

公开(公告)号：US20130261353A1

公开(公告)日：2013-10-03

申请号：US13432300

申请日：2012-03-28

Applicant: Konstantin A. Pokrovski ,  Daniel C. Merkel ,  Haiyou Wang ,  Hsueh Sung Tung

Inventor： Konstantin A. Pokrovski ,  Daniel C. Merkel ,  Haiyou Wang ,  Hsueh Sung Tung

IPC: C07C17/25

CPC classification number: C07C17/25 ,  C07C17/206 ,  C07C17/208 ,  C07C17/21 ,  C07C17/38 ,  C07C17/383 ,  C07C17/395 ,  Y02P20/125 ,  Y02P20/582 ,  C07C21/18 ,  C07C19/08

Abstract: Disclosed is an integrated manufacturing process to co-produce (E) 1-chloro-3,3,3-trifluoropropene, (E) 1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoro-propane starting from a single starting feed material or a mixture of unsaturated hydrochloro-carbon feed materials comprising 1,1,1,3-tetrachloropropene and/or 1,1,3,3-tetrachloro-propene. The process includes a combined liquid or vapor phase reaction/purification operation which directly produces (E) 1-chloro-3,3,3-trifluoro-propene (1233zd (E)) from these feed materials, which may also include 240fa. In the second liquid phase fluorination reactor 1233zd (E) is contacted with HF in the presence of catalyst to produce 1,1,1,3,3-pentafluoropropane (245fa) with high conversion and selectivity. A third reactor is used for dehydrofluorination of 245fa to produce (E) 1,3,3,3-tetrafluoro-propene (1234ze (E)) by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrofluorination catalyst. This operation may be followed by one or more purification processes to recover the 1234ze (E) product.

Abstract translation: 公开了共同生产（E）1-氯-3,3,3-三氟丙烯，（E）1,3,3,3-四氟丙烯和1,1,1,3,3-五氟 丙烷从单起始原料或包含1,1,1,3-四氯丙烯和/或1,1,3,3-四氯丙烯的不饱和氯碳 - 碳进料的混合物开始。 该方法包括从这些进料中直接生产（E）1-氯-3,3,3-三氟丙烯（1233zd（E））的液相或汽相反应/纯化操作，其也可以包括240fa。 在第二液相氟化反应器1233zd（E）中，在催化剂存在下与HF接触，得到具有高转化率和选择性的1,1,1,3,3-五氟丙烷（245fa）。 第三反应器用于245fa的脱氟化氢以通过使用脱氟化氢催化剂在液相中与苛性碱溶液或气相接触来制备（E）1,3,3,3-四氟丙烯（1234ze（E）） 。 该操作之后可以进行一个或多个纯化过程以恢复1234ze（E）产物。

公开(公告)号：US08546624B2

公开(公告)日：2013-10-01

申请号：US12396528

申请日：2009-03-03

Applicant: Hang T. Pham ,  Daniel C. Merkel ,  Konstantin A. Pokrovski ,  HsuehSung Tung ,  Rajiv R. Singh

Inventor： Hang T. Pham ,  Daniel C. Merkel ,  Konstantin A. Pokrovski ,  HsuehSung Tung ,  Rajiv R. Singh

IPC: C07C17/383

CPC classification number: C07C17/206 ,  C07C17/38 ,  C07C17/383 ,  C07C21/18

Abstract: Provided are azeotropic and azeotrope-like compositions of 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) and hydrogen fluoride (HF). Such azeotropic and azeotrope-like compositions are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).

Abstract translation: 提供2-氯-3,3,3-三氟丙烯（HCFO-1233xf）和氟化氢（HF）的共沸和类共沸组合物。 这种共沸和类共沸组合物可用作生产2,3,3,3-四氟丙烯（HFO-1234yf）的中间体。

公开(公告)号：US08373010B2

公开(公告)日：2013-02-12

申请号：US12875170

申请日：2010-09-03

Applicant: Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung ,  Selma Bektesevic

Inventor： Daniel C. Merkel ,  Konstantin A. Pokrovski ,  Hsueh Sung Tung ,  Selma Bektesevic

IPC: C07C17/25

CPC classification number: C07C17/25 ,  C07C17/206 ,  C07C17/354 ,  C07C21/18 ,  C07C19/08

Abstract: Disclosed is a process for the preparation of 3,3,3-trifluoropropene comprising the steps of; (1) fluorination of 240fa to form 245fa; (2) conversion of 245fa to a cis/trans mixture of 1234ze; (3) hydrogenation of the cis/trans mixture of 1234ze to form 254fb ; and (4) dehydrofluorination of 254fb to produce 3,3,3-trifluoropropene. Alternatively or additionally, a second process for the preparation of the desired compound comprises the following steps; (1) fluorination of HCC-240fa to form HCFC-244fa; (2) conversion of 244fa to a cis/trans mixture of HFO-1234ze; (3) hydrogenation of the cis/trans mixture of 1234ze to form HFC-254fb; and (4) dehydrofluorination of 254fb to produce 3,3,3-trifluoropropene.

Abstract translation: 公开了制备3,3,3-三氟丙烯的方法，包括以下步骤： （1）240fa的氟化以形成245fa; （2）将245fa转化为1234ze的顺式/反式混合物; （3）将1234ze的顺式/反式混合物氢化成254fb; 和（4）254fb的脱氟化氢，得到3,3,3-三氟丙烯。 或者或另外，制备所需化合物的第二种方法包括以下步骤： （1）HCC-240fa氟化形成HCFC-244fa; （2）将244fa转化为HFO-1234ze的顺式/反式混合物; （3）将1234ze的顺式/反式混合物氢化形成HFC-254fb; 和（4）254fb的脱氟化氢，得到3,3,3-三氟丙烯。

公开(公告)号：US20120310019A1

公开(公告)日：2012-12-06

申请号：US13587182

申请日：2012-08-16

Applicant: HAIYOU WANG ,  KONSTANTIN A. POKROVSKI ,  HSUEH S. TUNG ,  Michael Van Der Puy

Inventor： HAIYOU WANG ,  KONSTANTIN A. POKROVSKI ,  HSUEH S. TUNG ,  Michael Van Der Puy

IPC: C07C17/25 ,  C07C21/18

CPC classification number: C07C17/25 ,  C07B2200/09 ,  C07C17/087 ,  C07C17/358 ,  C07C17/383 ,  C07C21/18 ,  Y02P20/582 ,  C07C19/08

Abstract: The present invention involves methods for isomerization of 1234zc. Also provided are methods for managing 1,1,3,3-tetrafluoropropene produced as a byproduct in a process for synthesizing trans-1,3,3,3-tetrafluoropropene from 245fa, wherein 1234zc is converted into trans/cis-1234ze with the help of a catalyst in the absence of HF and in an isomerization reactor, or is converted into 1234zc and/or 245fa with the help of a catalyst in the presence of HF in a separate reactor or preferably in the same reactor of 245fa dehydrofluorination.

Abstract translation: 本发明涉及1234zc的异构化方法。 还提供了在用于从245fa合成反式-1,3,3,3-四氟丙烯的方法中管理作为副产物生产的1,1,3,3-四氟丙烯的方法，其中1234zc被转化成反式/顺式1234ze， 在不存在HF的情况下和在异构化反应器中的催化剂的帮助下，或者在HF存在下，在单独的反应器中，或优选在245fa脱氟化氢的相同反应器中，借助催化剂将其转化为1234zc和/或245fa。